Insecticidal phthalamide derivatives

ABSTRACT

This invention relates to novel insecticidal phthalamide derivatives of formula (I)  
                 
         in which X, n, Y, m, R 1 , R 2 , R 3 , A 1 , r, A 2 , s, Q and E have the meanings given in the disclosure, to a plurality of processes for preparing these compounds, and to their use for controlling pests.

The present invention relates to novel phthalamide derivatives; toprocesses for their preparation and to their use as insecticides.

Certain phthalamide derivatives showing an action as insecticide arealready known (cf. EP-A 0 919 542, WO 01/00575, JP-A 2001-64268, EP-A 1006 107, JP-A 2003-40864, WO 01/21576 and WO 03/11028). Further, it isalready known that certain phthalamide derivatives show an action aspharmaceutical (cf. EP-A 0 119 428).

The conventional phthalamide derivatives, however, are not fullysatisfactory in terms of effects as insecticide.

There have now been found novel phthalamide derivatives of the followingformula (I)

wherein

-   X represents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, nitro,    cyano, C₁-C₆-alkylsulfonyloxy, C₁-C₆-haloalkylsulfonyloxy,    phenylsulfonyloxy, C₁-C₆-alkylthio-C₁-C₆-alkyl,    C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl,    C₁-C₆-alkylsulfonylamino, bis(C₁-C₆-alkylsulfonyl)amino or    C₁-C₆-alkylcarbonyloxy,-   n represents 1, 2, 3 or 4,-   Y represents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₁-C₆-alkoxy, C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio    or cyano,-   m represents 1, 2, 3 or 4,-   R¹ represents C₁-C₈-alkyl, C₁-C₈-alkyl which is mono- or    poly-substituted by substituents selected from the group consisting    of cyano, nitro, C₁-C₆-alkylaminosulfonyl,    N,N-di(C₁-C₆-alkyl)aminosulfonyl, C₁-C₆-alkylsulfonylamino,    N—C₁-C₆-alkylsulfonyl-N-C₁-C₆-alkylamino, C₁-C₆-alkyl-carbonylamino,    halo-C₁-C₆-alkyl, N—C₁-C₆-alkyl-carbonyl-N-C₁-C₆-alkylamino,    C₁-C₆-alkyl-thiocarbonylamino,    N—C₁-C₆-alkylthiocarbonyl-N—C₁-C₆-alkylamino,    C₁-C₆-alkoxyimino-C₁-C₆-alkyl, C₁-C₆-alkyl-aminocarbonyl,    N,N-di(C₁-C₆-alkyl)-aminocarbonyl, C₁-C₆-alkyl-aminothiocarbonyl,    N,N-di(C₁-C₆-alkyl)-aminothiocarbonyl, C₁-C₆-alkoxy-carbonylamino,    C₁-C₆-alkoxy-carbonyl-C₁-C₆-alkylamino,    C₁-C₆-alkylamino-carbonyloxy, N,N-di(C₁-C₆-alkyl)amino-carbonyloxy,    C₁-C₆-alkoxy-thiocarbonylamino,    C₁-C₆-alkoxy-thiocarbonyl-C₁-C₆-alkylamino,    C₁-C₆-alkylamino-thiocarbonyloxy,    N,N-di(C₁-C₆alkyl)-amino-thiocarbonyloxy,    C₁-C₆-alkylthio-carbonylamino,    C₁-C₆-alkylthio-carbonyl-C₁-C₆-alkylamino,    C₁-C₆-alkylamino-carbonylthio,    N,N-di(C₁-C₆-alkyl)amino-carbonylthio,    C₃-C₆-alkylthio-thiocarbonylamino,    C₁-C₆-alkylthio-thiocarbonyl-C₁-C₆-alkylamino,    C₁-C₆-alkylamino-thiocarbonylthio,    N,N-di(C₁-C₆-alkyl)amino-thiocarbonylthio, C₃-C₆-cycloalkyl,    C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl,    C₁-C₆-alkylsulfinyl-C₁-C₆-allyl and C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl,    or represents C₃-C₈-cycloalkyl which may be substituted by    substituents selected from the group consisting of C₁-C₄-alkyl,    C₁-C₄-alkylthio or C₁-C₂-alkylthio-C₁-C₂-alkyl,-   R² represents hydrogen or C₁-C₆-alkyl,-   R³ represents hydrogen or C₁-C₆-alkyl,-   A¹ represents straight chain or branched chain C₁-C₈-alkylene,    C₁-C₈-haloalkylene, C₂-C₈-alkenylene, C₂-C₈-haloalkenylene,    C₂-C₈-alkynylene, C₂-C₈-haloalkynylene, C₁-C₈-alkylene-amino,    C₁-C₈-alkylene(C₁-C₆-alkylamino), C₁-C₈-alkyleneoxy or    C₁-C₈-alkylenethio,-   r represents 0 or 1,-   A² represents straight chain or branched chain C₁-C₈-alkylene,    C₂-C₈-haloalkylene, C₂-C₈-alkenylene, C₂-C₈-haloalkenylene,    C₂-C₈-alkynylene or C₂-C₈-haloalkynylene,-   s represents 0 or 1,-   Q represents a 5- or 6-membered heterocyclic group containing 1 to 4    hetero atoms selected from 0 to 4 nitrogen atom, 0 to 1 oxygen atom,    and 0 to 1 sulphur atom, however not containing an oxygen atom and a    sulphur atom at the same time, and said heterocyclic group may have    one to three    one to three    one    or one-    as ring constituent, and said heterocyclic group may be optionally    substituted with at least one or more substituents selected from the    below-mentioned group of substituents W¹ wherein said substituents    may be identical or different,-   W¹ represents halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,    C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl,    C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio, C₁-C₆-haloalkylsulfinyl,    C₁-C₆-haloalkylsulfonyl, C₃-C₆-Cycloalkyl,    C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl,    C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl,-   E represents phenyl, biphenyl, naphthyl, pyridyl, pyridazinyl,    pyrimidinyl, pyrazinyl, thienyl, furyl or pyrrolyl, wherein said    group is optionally mono- or poly-substituted by substituents    selected from the group W² wherein said substituents may be    identical or different,-   W² represents halogen, nitro, C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,    C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio,    C₁-C₆-haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆-cycloalkyl,    C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl or    C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, or represents C₃-C₅-allylene,    C₃-C₅-haloalkylene, oxy-C₂-C₄-alkylene, oxy-C₂-C₄-haloalkylene,    C₂-C₄-alkyleneoxy, C₁-C₄-haloalkyleneoxy, C₁-C₃-alkylenedioxy or    C₁-C₃-haloalkylenedioxy, in case that W² are two adjacent    substituents.

Depending, if appropriate, on the type and number of substituents, thecompounds of the formula (I) can be present as geometrical and/oroptical isomers, regioisomers and/or configurational isomers or isomermixtures thereof of varying composition. What is claimed by theinvention are both the pure isomers and the isomer mixtures.

The compounds of the formula (I) of the present invention can beobtained, for example, by the following preparation processes (a), (b),(c), (d), (e) and (f):

Preparation Process (a): in case that R² in the Formula (I) RepresentsHydrogen.

-   -   A process of reacting compounds of the formula (II)    -   wherein R¹, X and n have the same definition as aforementioned,    -   with compounds of the formula all)    -   wherein R³, Y, m, A¹, r, Q, A², s and E have the same definition        as aforementioned, in the presence of inert solvents.        Preparation Process (b): in Case that R³ in the Formula (I)        Represents Hydrogen Atom.    -   A process of reacting compounds of the formula (IV)    -   wherein X, n, Y, m, A¹, r, Q, A², s and E have the same        definition as aforementioned, with compounds of the formula (V)    -   wherein R¹ and R² have the same definition as aforementioned,    -   in the presence of inert solvents, and if appropriate, in the        presence of a base.        Preparation Process (c):    -   A process of reacting a compound represented by the formula (VI)    -   wherein X, n, R¹ and R² have the same definition as        aforementioned,    -   with the compounds of the formula (III),    -   wherein R³, Y, m, A¹, r, Q, A², s and E have the same definition        as aforementioned, in the presence of inert solvents.        Preparation Process (d): in Case that R³ in the Formula (I)        Represents Hydrogen Atom.    -   A process of reacting compounds of the formula (VII)    -   wherein X, n, Y, m, A¹, r, Q, A², s and E have the same        definition as aforementioned, with the compounds of the formula        (V),    -   wherein R¹ and R² have the same definition as aforementioned,    -   in the presence of inert solvents.        Preparation Process (e):    -   A process of reacting a compounds of the formula (VIII)    -   wherein X, n, R³, Y, m, A¹, r, Q, A², s and E have the same        definition as aforementioned, with the compounds of the formula        (V),    -   wherein R¹ and R² have the same definition as aforementioned,    -   in the presence of inert solvents.        Preparation Process (f): in Case that R¹ in the Formula (I)        Represents C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl or        C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl.    -   A process of reacting compounds of the formula (If)    -   wherein R^(1f) represents C₁-C₆-alkylthio-C₁-C₆-alkyl, and    -   X, n, R², R³, Y, m, A¹, r, Q, A², s and E have the same        definition as aforementioned, with an oxidizing agent in the        presence of inert solvents.

According to the present invention, the phthalamide derivatives of theaforementioned formula (a) show strong insecticidal action.

The formula (I) provides a general definition of the phthalamidederivatives according to the invention.

Preferred substituents or ranges of radicals listed in the formulaementioned above and below are illustrated below:

-   X preferably represents hydrogen, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, nitro, cyano, C₁-C₄-alkylsulfonyloxy,    C₁-C₄-haloalkylsulfonyloxy, phenylsulfonyloxy, C₁-C₄-alkylthio-C₁-C₄    alkyl, C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl,    C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₄-alkylsulfonylamino,    bis(C₁-C₄-alkylsulfonyl)amino or C₁-C₄-alkylcarbonyloxy.-   X particularly preferably represents hydrogen, fluorine, chlorine,    bromine, iodine, methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or    tert-butyl, trifluoromethyl, difluoromethyl, dichlorofluoromethyl,    trichloromethyl, nitro, cyano, methylsulfonyloxy, ethylsulfonyloxy,    trifluoromethylsulfonyloxy, phenylsulfonyloxy, methylthiomethyl,    methylthioethyl, ethylthiomethyl, ethylthioethyl,    methylsulfinylmethyl, methylsulfinylethyl, ethylsulfinylmethyl,    ethylsulfinylethyl, methylsulfonylmethyl, methylsulfonylethyl,    ethylsulfonylmethyl, ethylsulfonylethyl, methylsulfonylamino,    ethylsulfonylamino, di(methylsulfonyl)amino, di(ethylsulfonyl)amino,    methylcarbonyloxy or ethylcarbonyloxy.-   X very particularly preferably represents hydrogen, fluorine,    chlorine, bromine, iodine, methyl, tert-butyl, trifluoromethyl,    nitro, cyano, methylsulfonyloxy, ethylsulfonyloxy,    trifluoromethylsulfonyloxy, phenylsulfonyloxy, methylsulfonylamino,    di(methylsulfonyl)amino or methylcarbonyloxy.-   n preferably represents 1, 2 or 4.-   n particularly preferably represents 1.-   n furthermore, particularly preferably represents 2.-   n furthermore, particularly preferably represents 4.-   Y preferably represents hydrogen, halogen, C₁-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-haloalkylthio or cyano.-   Y particularly preferably represents hydrogen, fluorine, chlorine,    bromine, methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or    tert-butyl, trifluoromethyl, difluoromethyl, dichlorofluoromethyl,    trichloromethyl, methoxy, ethoxy, n- or iso-propoxy, n-, sec-, iso-    or tert-butoxy, trifluoromethoxy, methylthio, ethylthio, n- or    iso-propylthio, n-, sec-, iso- or tert-butylthio,    trifluoromethylthio or cyano.-   Y very particularly preferably represents hydrogen, chlorine,    methyl, trifluoromethyl, methoxy or trifluoromethoxy.-   m preferably represents 1 or 2.-   m particularly preferably represents 1.-   m furthermore, particularly preferably represents 2.-   R¹ preferably represents C₁-C₆-alkyl, C₁-C₆-alkyl which is mono- or    poly-substituted by substituents selected from the group consisting    of cyano, nitro, C₁-C₄-alkylaminosulfonyl,    N,N-di(C₁-C₄-alkyl)aminosulfonyl, C₁-C₄-alkylsulfonylamino,    N—C₁-C₄-alkylsulfonyl-N—C₁-C₄-alkylamino, C₁-C₄-alkyl-carbonylamino,    halo-C₁-C₄-alkyl, N—C₁-C₄-alkyl-carbonyl-N—C₁-C₄-alkylamino,    C₁-C₄-alkyl-thiocarbonylamino,    N—C₁-C₄-alkylthiocarbonyl-N—C₁-C₄-alkylamino,    C₁-C₄-alkoxyimino-C₁-C₄-alkyl, C₁-C₄-alkyl-aminocarbonyl,    N,N-di(C₁-C₄-alkyl) aminocarbonyl, C₁-C₄-alkyl-aminothiocarbonyl,    N,N-di(C₁-C₄-alkyl)-aminothiocarbonyl, C₁-C₄-alkoxy-carbonylamino,    C₁-C₄-alkoxy-carbonyl-C₁-C₄-alkylamino,    C₁-C₄-alkylamino-carbonyloxy, N,N-di(C₁-C₄-alky)amino-carbonyloxy,    C₁-C₄-alkoxy-thiocarbonylamino,    C₁-C₄-alkoxy-thiocarbonyl-C₁-C₄-alkylamino,    C₁-C₄-alkylamino-thiocarbonyloxy,    N,N-di(C₁-C₄-alkyl)amino-thiocarbonyloxy,    C₁-C₄-alkylthio-carbonylamino,    C₁-C₄-alkylthio-carbonyl-C₁-C₄-alkylamino,    C₁-C₄-alkylamino-carbonylthio,    N,N-di(C₁-C₄-alkyl)amino-carbonylthio,    C₁-C₄-alkylthio-thiocarbonylamino,    C₁-C₄-alkylthio-thiocarbonyl-C₁-C₄-alkylamino,    C₁-C₄-alkylamino-thiocarbonylthio,    N,N-di(C₁-C₄-alkyl)amino-thiocarbonylthio, C₃-C₆-cycloalkyl,    C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,    C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl and C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl,    or represents C₃-C₆-cycloalkyl which may be substituted by    C₁-C₂-alkyl, C₁-C₂-alkylthio or C₁-C₂-alkylthio-C₁-C₂-alkyl.-   R¹ particularly preferably represents methyl, ethyl, n- or    iso-propyl, n-, sec-, iso- or tert-butyl, n-pentyl, 1-methylbutyl,    1-ethylpropyl, n-hexyl, 1,3-dimethylbutyl; methyl, ethyl, n- or    iso-propyl, n-, sec-, iso- or tert-butyl, each of which is mono- or    poly-substituted by substituents selected from the group consisting    of cyano, nitro, methylaminosulfonyl, ethylaminosulfonyl,    N,N-di(methyl)aminosulfonyl, N,N-di(ethyl)aminosulfonyl,    methylsulfonylamino, ethylsulfonylamino,    N-methylsulfonyl-N-methylamino, N-ethylsulfonyl-N-methylamino,    N-methylsulfonyl-N-ethylamino, N-ethylsulfonyl-N-ethylamino,    methyl-carbonylamino, ethyl-carbonylamino, trifluoromethyl,    pentafluoroethyl, N-methyl-carbonyl-N-methylamino,    methylthio-carbonylamino, ethyl-thiocarbonylamino,    N-methylthiocarbonyl-N-methylamino, methoxyimino-methyl,    methoxyimino-ethyl, ethoxyimino-methyl, ethoxyimino-ethyl,    methylaminocarbonyl, ethyl-aminocarbonyl,    N,N-di(methyl)-aminocarbonyl, N,N-di(ethyl)-aminocarbonyl,    methyl-aminothiocarbonyl, ethyl-aminothiocarbonyl,    N,N-di(methyl)-aminothiocarbonyl, N,N-di(ethyl)-aminothiocarbonyl,    methoxy-carbonylamino, ethoxy-carbonylamino,    methoxy-carbonyl-methylamino, ethoxy-carbonyl-methylamino,    methoxy-carbonyl-ethylamino, ethoxy-carbonyl-ethylamino,    methylamino-carbonyloxy, ethylamino-carbonyloxy,    N,N-di(methyl)amino-carbonyloxy, N,N-di(ethyl)amino-carbonyloxy,    methoxy-thiocarbonylamino, ethoxy-thiocarbonylamino,    methoxy-thiocarbonyl-methylamino, methoxy-thiocarbonyl-ethylamino,    ethoxy-thiocarbonyl-methylamino, ethoxy-thiocarbonyl-ethylamino,    methylamino-thiocarbonyloxy, ethylamino-thiocarbonyloxy,    N,N-di(methyl)amino-thiocarbonyloxy,    N,N-di(ethyl)amino-thiocarbonyloxy, methylthio-carbonylamino,    ethylthio-carbonylamino, methylthio-carbonyl-methylamino,    ethylthio-carbonyl-methylamino, methylthio-carbonyl-ethylamino,    ethylthio-carbonyl-ethylamino, methylamino-carbonylthio,    ethylamino-carbonylthio, N,N-di(methyl)amino-carbonylthio,    N,N-di(ethyl)amino-carbonylthio, methylthio-thiocarbonylamino,    ethylthio-thiocarbonylamino, methylthio-thiocarbonyl-methylamino,    ethylthio-thiocarbonyl-methylamino,    methylthio-thiocarbonyl-ethylamino,    ethylthio-thiocarbonyl-ethylamino, methylamino-thiocarbonylthio,    ethylamino-thiocarbonylthio, N,N-di(methyl)amino-thiocarbonylthio,    N,N-di(methyl)amino-thiocarbonylthio, cyclopropyl, cyclopentyl,    cyclohexyl, methoxy-methyl, ethoxy-methyl, methoxy-ethyl,    ethoxy-ethyl, methylthiomethyl, ethylthio-methyl, methylthio-ethyl,    ethylthio-ethyl, methylsulfinyl-methyl, ethylsulfinyl-methyl,    methylsulfinyl-ethyl, ethylsulfinyl-ethyl, methylsulfonyl-methyl,    ethylsulfonylmethyl, methylsulfonyl-ethyl, and ethylsulfonyl-ethyl;    or represents cyclopropyl, cyclopentyl, cyclohexyl, each of which    may be substituted by substituents selected from the group    consisting of methyl, ethyl, methylthio, ethylthio,    methylthiomethyl, ethylthiomethyl, methylthioethyl and    ethylthioethyl.-   R¹ very particularly preferably represents methyl, ethyl, n- or    iso-propyl, n- or sec-butyl, n-pentyl, 1-methylbutyl, 1-ethylpropyl,    1,3-dimethylbutyl; methyl, ethyl, n- or iso-propyl, n-, sec-, iso-    or tert-butyl, each of which is mono- or poly-substituted by    substituents selected from the group consisting of cyano,    methylaminosulfonyl, ethylaminosulfonyl,    N,N-di(methyl)aminosulfonyl, N,N-di(ethyl)aminosulfonyl,    N-methylsulfonyl-N-methylamino, methyl-carbonylamino,    trifluoromethyl, pentafluoroethyl, methoxyimino-methyl,    methoxyimino-ethyl, ethoxyimino-methyl, ethoxyimino-ethyl,    methyl-aminocarbonyl, ethyl-aminocarbonyl,    N,N-di(methyl)-aminocarbonyl, N,N-di(ethyl)-aminocarbonyl,    methyl-aminothiocarbonyl, ethyl-aminothiocarbonyl,    N,N-di(methyl)-aminothiocarbonyl, N,N-di(ethyl)-aminothiocarbonyl,    methoxy-carbonylamino, methylamino-carbonyloxy,    ethylamino-carbonyloxy, N,N-di(methyl)amino-carbonyloxy,    N,N-di(ethyl)amino-carbonyloxy, methylamino-thiocarbonyloxy,    N,N-di(methyl)amino-thiocarbonyloxy, methylamino-carbonylthio,    ethylamino-carbonylthio, methylamino-thiocarbonylthio,    ethylamino-thiocarbonylthio, cyclohexyl, methoxy-methyl,    ethoxy-methyl, methylthio-methyl, methylsulfinyl-methyl and    methylsulfonyl-methyl; or cyclopropyl, cyclopentyl, cyclohexyl, each    of which may be substituted by substituents selected from the group    consisting of methyl, methylthio and methylthiomethyl.-   R² preferably represents hydrogen or C₁-C₄-alkyl.-   R² particularly preferably represents hydrogen, methyl or ethyl.-   R² very particularly preferably represents hydrogen or ethyl.-   R³ preferably represents hydrogen or C₁-C₄-alkyl.-   R³ particularly preferably represents hydrogen, methyl, ethyl, n- or    iso-propyl.-   R³ very particularly preferably represents hydrogen, methyl, ethyl    or iso-propyl.-   A¹ preferably represents straight chain or branched chain    C₁-C₆-alkylene, C₁-C₆-haloalkylene, C₂-C₆-alkenylene,    C₂-C₆-haloalkenylene, C₂-C₆-alkynylene, C₂-C₆-haloalkynylene,    C₁-C₆-alkylene-amino, C₁-C₆-alkylene(C₁-C₄-alkylamino),    C₁-C₆-alkyleneoxy or C₁-C₆-alkylenethio.-   A¹ particularly preferably represents —CH₂—, —(CH₂)₂—, —(CH₂)₃—,    —CH(CH₃)—, —OCH₂—, —CH₂O—, —O(CH₂)₂—, —(CH₂)₂O—, —CH₂—, —CH₂S—,    —S(CH₂)₂— or —(CH₂)₂S—.-   A¹ very particularly preferably represents —CH₂—, —(CH₂)₂—,    —CH(CH₃)—, —OCH₂—, —O(CH₂)₂— or —CH₂S—.-   r preferably represents 0.-   r furthermore preferably represents 1.-   A² preferably represents straight chain or branched chain    C₁-C₆-alkylene, C₁-C₆-haloalkylene, C₂-C₆-alkenylene,    C₂-C₆-haloalkenylene, C₂-C₆-alkynylene or C₂-C₆-haloalkynylene.-   A² particularly preferably represents —CH₂—, —(CH₂)₂—, —(CH₂)₃—,    —CH(CH₃)—, —CH₂—CH═CH—.-   s preferably represents 0.-   s furthermore preferably represents 1.-   Q preferably represents pyridinylene, pyridazinylene,    pyrimidinylene, pyrazinylene, each of which is optionally mono- or    poly-substituted by substituents selected from group W¹ wherein said    substituents may be identical or different, or further represents    the below-mentioned groups;-    (wherein the bond marked with * connects with A¹ and the bond    marked with # connects with A², or the bond marked with # connects    with A¹ and the bond marked with * connects with A²)-   Q particularly preferably represents Q15, Q17, Q22, Q23, Q29, Q34,    Q35, Q45, Q48, Q50, Q55, Q56, Q58, Q59, Q60, Q61, Q62, Q63, Q64, Q66    and Q69.-   Q very particularly preferably represents Q15.-   Q furthermore very particularly preferably represents Q17.-   Q furthermore very particularly preferably represents Q22.-   Q furthermore very particularly preferably represents Q23.-   Q furthermore very particularly preferably represents Q29.-   Q furthermore very particularly preferably represents Q34.-   Q furthermore very particularly preferably represents Q35.-   Q furthermore very particularly preferably represents Q45.-   Q furthermore very particularly preferably represents Q48.-   Q furthermore very particularly preferably represents Q50.-   Q furthermore very particularly preferably represents Q55.-   Q furthermore very particularly preferably represents Q56.-   Q furthermore very particularly preferably represents Q58.-   Q furthermore very particularly preferably represents Q59.-   Q furthermore very particularly preferably represents Q60.-   Q furthermore very particularly preferably represents Q61.-   Q furthermore very particularly preferably represents Q62.-   Q furthermore very particularly preferably represents Q63.-   Q furthermore very particularly preferably represents Q64.-   Q furthermore very particularly preferably represents Q66.-   Q furthermore very particularly preferably represents Q69.-   W¹ preferably represents halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,    C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl    C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl,    C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl.-   W¹ particularly preferably represents methyl, ethyl, methoxy,    methylthio, methylsulfinyl or methylsulfonyl.-   W¹ very particularly preferably represents methyl.-   E preferably represents phenyl, biphenyl, naphthyl, pyridyl,    pyridazinyl, pyrimidinyl, pyrazinyl, thienyl, furyl or pyrrolyl,    wherein said group is optionally mono- or poly-substituted by    substituents selected from the group W² wherein said substituents    may be identical or different.-   E particularly preferably represents phenyl, biphenyl, 3-pyridyl,    2-thienyl, 2-furyl or 2-pyrrolyl, wherein said group is optionally    mono- to tetra-substituted by substituents selected from the group    W² wherein said substituents may be identical or different-   E very particularly preferably represents phenyl, biphenyl,    3-pyridyl or 2-thienyl, wherein said group is optionally mono- to    tetra-substituted by substituents selected from the group W² wherein    said substituents may be identical or different.-   W² preferably represents halogen, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,    C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₃-C₆-cycloalkyl,    C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl or    C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, or represents C₃-C₅-alkylene,    C₃-C₅-haloalkylene, oxy-C₂-C₄-alkylene, oxy-C₂-C₄-haloalkylene,    C₂-C₄-alkyleneoxy, C₂-C₄-haloalkyleneoxy, C₁-C₃-alkylenedioxy or    C₁-C₄-haloalkylenedioxy, in case W² are two adjacent substituents.-   W² particularly preferably represents fluorine, chlorine, bromine,    nitro, methyl, ethyl, n- or iso-propyl, n-, sec-, iso- or    tert-butyl, methoxy, ethoxy, n- or iso-propoxy, n-, see-, iso- or    tert-butoxy, trifluoromethoxy, difluoromethoxy, methylthio,    ethylthio, n- or iso-propylthio, n-, sec-, iso- or tert-butylthio,    trifluoromethyl, difluoromethyl, dichlorofluoromethyl,    trichloromethyl, trifluoromethoxy, difluoromethoxy,    trifluoromethylthio, or represents —OCF₂O—, —O(CF₂)₂O—, —OCHFCF₂O—,    —OCF₂CHFO—, in case W² are two adjacent substituents.-   W² very particularly preferably represents fluorine, chlorine,    bromine, nitro, methyl, ethyl, iso-propyl, methoxy,    trifluoromethoxy, difluoromethoxy, methylthio, trifluoromethylthio,    or represents —OCF₂O—, —O(CF₂)₂O—, —OCHFCF₂O—, —OCF₂CHFO—, in case    W² are two adjacent substituents.-   W³ represents hydrogen or has the same definition as the    aforementioned W¹,-   W³ preferably represents hydrogen, methyl, trifluoromethyl or    methylthio.-   p represents 0, 1 or 2.-   p preferably represents 0.-   p furthermore preferably represents 1.-   q represents 0, 1, 2 or 3.-   q preferably represents 0.-   q furthermore preferably represents 1.

Compounds of formula (I), in which r is 0 and s is 0 are preferred.

Compounds of formula (I), in which r is 1 and s is 1 are preferred.

Compounds of formula (I), in which r is 1 and s is 9 are particularlypreferred.

Compounds of formula (I), in which R² and R³ are both hydrogen arepreferred.

Compounds of formula (I), in which n is 1 and X is located in 3-positionare preferred.

Compounds of formula (I), in which X is iodine are preferred.

Compounds of formula (I), in which Y is methyl are preferred.

Compounds of formula (I), in which A¹ is —CH₂— are preferred.

Compounds of formula (I), in which E is mono- to tetra-substitutedphenyl, where the substituents are selected from the group W², arepreferred.

Compounds of formula (I), in which Q is Q66 are preferred.

The general or preferred radical definitions or illustrations listedabove apply both to the end products and, correspondingly, to thestarting materials and intermediates. These radical definitions can becombined with one another as desired, i.e. including combinationsbetween the respective preferred ranges.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred.

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

In the radical definitions given above and below, carbon radicals, suchas alkyl, are in each case straight-chain or branched as far as this ispossible—including in combination with hetero atoms such as alkoxy.

The aforementioned preparation process (a) can be illustrated by thefollowing reaction scheme in case, for example, that3-(1,1-dimethyl-2-methylthioethylimino)-4-iodo-3H-isobenzofuran-1-oneand1-(4-amino-3-methylbenzyl)-4-(4-trifluoromethylphenyl)-1,4-dihydrotetrazol-5-oneare used as starting materials.

The aforementioned preparation process (b) can be illustrated by thefollowing reaction scheme in case, for example, that2-{2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-1-ylmethyl]phenyl}isoindole-1,3-dioneand sec-butylamine are used as starting materials.

The aforementioned preparation process (c) can be illustrated by thefollowing reaction scheme in case, for example, thatN-(1-methyl-propyl)phthalamic acid and1-(4-amino-3-methylbenzyl)-4-(4-trifluoromethylphenyl)-1,4-dihydrotetrazol-5-oneare used as starting materials.

The aforementioned preparation process (d) can be illustrated by thefollowing reaction scheme in case, for example, that1-[4-(3-oxo-3H-isobenzofuran-1-ylideneamino)-3-methyl-benzyl]-4-(4-trifluoromethyl-phenyl)-1,4-dihydrotetrazol-5-oneand sec-butylamine are used as starting materials.

The aforementioned preparation process (e) can be illustrated by thefollowing reaction scheme in case, for example, thatN-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydrotetrazol-1-ylmethyl]-phenyl}-phthalamicacid and sec-butylamine are used as starting materials.

The aforementioned preparation process (f) can be illustrated by thefollowing reaction scheme in case, for example, thatN²-(1,1-dimethyl-2-methylthioethyl)-3-iodo-N¹-[2-methyl-4-(5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl)-phenyl]-phthalamideand m-chloroperbenzoic acid are used as starting materials.

The compounds of the formula (II), starting material in theabove-mentioned preparation process (a), are per se known compounds andcan be easily prepared according to the process described in, forexample, EP-A 0 919 542, EP-A 1 006 107.

As specific examples of the compounds of the formula (I) used asstarting material in the preparation process (a) there can be mentionedthe following:

-   3-isopropylimino-3H-isobenzofuran-1-one,-   4-fluoro-3-isopropylimino-3H-isobenzofuran-1-one,-   4-chloro-3-isopropylimino-3H-isobenzofuran-1-one,-   4-bromo-3-isopropylimino-3H-isobenzofuran-1-one,-   4-iodo-3-isopropylimino-3H-isobenzofuran-1-one,-   3-isopropylimino-nitro-3H-isobenzofuran-1-one,-   3-isopropylimino-5-nitro-3H-isobenzofuran-1-one,-   3-(1-methyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   4-fluoro-3-(1-methyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   4-chloro-3-(1-methyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   4-bromo-3-(1-methyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   4-iodo-3-(1-methyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   3-(1-methyl-2-methylsulfanyl-ethylimino)-4-nitro-3H-isobenzofuran-1-one,-   3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-4-fluoro-3H-isobenzofuran-1-one,-   4-chloro-3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   4-bromo-3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-4-iodo-3H-isobenzofuran-1-one,-   3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-4-nitro-3H-isobenzofuran-1-one,-   3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-4-methyl-3H-isobenzofuran-1-one,-   3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-5-methyl-3H-isobenzofuran-1-one,-   4,7-dichloro-3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   5,6-dichloro-3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   4,5,6,7-tetrachloro-3-(1,1-dimethyl-2-methylsulfanyl-ethylimino)-3H-isobenzofuran-1-one,-   3-isopropylimino-1-oxo-1,3-dihydro-isobenzofuran-4-yl    methanesulfonate,-   3-(1-methyl-2-methylsulfanyl-ethylimino-1-oxo-1,3-dihydro-isobenzofuranyl    methanesulfonate,-   3-(1,1-dimethyl-2-methylsulfanyl-ethylimino-1-oxo-1,3-dihydro-isobenzofuran-4-yl    methanesulfonate.

The compounds of the formula (E), starting material in theabove-mentioned preparation process (a), include novel compounds notmentioned in the existing literature as a part.

Their corresponding anilines can be obtained, for example, by acatalytic hydrogen reduction, a well-known process in the field oforganic chemistry, by reducing compounds of the formula

wherein Y, m, A¹, r, Q, A², s and E have the same definitions asaforementioned with hydrogen in the presence of a catalytic reductioncatalyst, for example, palladium carbon, Raney nickel, platinum oxide.

Compounds of the formula (III), in which R³ corresponds alkyl, can beobtained by formylating the amino group of the anilines, furtheralkylating and then de-formylating. Moreover, compounds of the formula(E), in which R³ corresponds alkyl, can also be obtained by preparing aSchiff base complex by a reaction of the anilines obtained by thereduction of compounds of the formula QX) and a ketone or an aldehydeand then by catalytically reducing it.

The compounds of the above-mentioned formula (DC) are, as will bedescribed later in detail, novel compounds.

As specific examples of the compounds of the formula (Il) there can bementioned, for example,

-   1-(4-amino-3-methyl-benzyl)-1H-pyrazole,-   1-(4-amino-3-methyl-benzyl)-3-methyl-1H-pyrazole,-   1-(4-amino-3-methyl-benzyl)-4-methyl-1H-pyrazole,-   1-(4-amino-3-methyl-benzyl)-4,5-dichloro-1H-imidazole,-   1-(4-amino-3-methyl-benzyl)-1H-1,2,3-triazole,-   1-(4-amino-3-methyl-benzyl)-1H-1,2,4-triazole,-   1-(4-amino-3-methyl-benzyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-methyl-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(2-chloro-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(3-trifluoromethyl-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(4-trifluoromethyl-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(3,5-bis-trifluoromethyl-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(3-trifluoromethoxy-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolydin-2-one,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-1,3-dihydro-imidazol-2-one,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolydin-2,4-dione,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolydin-2,4,5-trione,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-1H-pyrazole,-   4-(4-amino-3-methyl-benzyl)-2-(2-fluoro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(2-chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(2-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(3-fluoro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(3-chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(3-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-fluoro-phenyl)-4-(4-amino-3-methyl-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(4-chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   (4-amino-3-methyl-benzyl)-2-(3,4-bis-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(3,5-bis-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-5-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)-4-(2-chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)-5-methyl-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)-4-(2-chloro-phenyl)-5-methylsulfanyl-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)-5-methylsulfanyl-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   1-(4-amino-3-methyl-benzyl)-4-methyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-methyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-propyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-isobutyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,2,2-trifluoro-ethyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4,4,4-trifluoro-butyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-(3,3,3-trichloro-2-methyl-propyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)cyclopropyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-cyclohexyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-phenyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-benzyl)-4-(2-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(4-amino-3-methyl-phenyl)-ethyl]-4-(2-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-methoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-benzyl)-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-difluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-bromo-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-isopropyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-2-chloro-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-chloro-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-difluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethoxy-sulfanyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3′,5-bis-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3′,5′-bis-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-bromo-2-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-fluoro-3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-bromo-4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-chloro-4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-fluoro-3-fluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-fluoro-5-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-chloro-3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,4-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,4-bis-fluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-fluoro-5-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,5-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,5-dimethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-2-chloro-benzyl)-4-(3,5-bis-fluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-chloro-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-2-methoxy-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrol-5-one,-   1-(4-amino-3-methoxy-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3,5-dimethyl-benzyl)-4-(3,5-bis-fluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(4-amino-3-methyl-phenyl)-ethyl]-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-chloro-2-methoxy-5-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydrotetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)    (2,2,3-trifluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydrotetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-(2,3,3-trifluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydrotetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,2,3,3,7-pentafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,5-dichloro-2,6-diethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-benzyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-fluoro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(2-fluoro-phenyl)ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[2-chloro-phenyl)ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(2-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(3-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(3-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(3-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(4-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(4-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-ammo-3-methyl-benzyl)-4-[1-(4-fluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(2,4-difluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(2,4-dichloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(3,4-difluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one.

The compounds of the formula (I), starting materials in theabove-mentioned preparation process (b), are novel ones and can beeasily obtained according to the process described in JP-A 61-246161,for example,by reacting a compound represented by the formula

wherein X and n have the same definition as aforementioned,with the compounds of the aforementioned formula (M)

in which R³ represents a hydrogen atom and Y, m, A¹, r, Q, A², s and Ehave the same definitions as aforementioned.

The reaction can be conducted in an adequate diluent. As examples of thediluent used in that case there can be mentioned aliphatic, alicyclicand aromatic hydrocarbons (may be optionally chlorinated), for example,pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene,toluene, xylene, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example,ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane,dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethylether (DGM); esters, for example, ethyl acetate, amyl acetate; acidamides, for example, dimethylformamide (DMF), dimethylacetamide (DMA),N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, hexamethylphosphoric triamide (HMPA); acids, for example, acetic acid.

The reaction can be conducted in a substantially wide range oftemperature. It can be conducted at the temperatures in a range ofgenerally room temperature to about 200° C., preferably room temperatureto 150° C.

Although said reaction is conducted desirably under normal pressure, itcan be operated also under elevated pressure or under reduced pressure.

In conducting the reaction, the aimed compounds can be obtained, forexample, by reacting equimolar amount or a little excess amount of thecompounds of the formula (III) to 1 mole of the compounds of the formula(X) in a diluent, for example, acetic acid.

Many of the compounds of the above-mentioned formula (X) are known(available on the market) compounds and as their specific examples therecan be mentioned, phthalic anhydride,

-   3-fluorophthalic anhydride,-   3-chlorophthalic anhydride,-   3-bromophthalic anhydride,-   3-iodophthalic anhydride,-   3-methylphthalic anhydride,-   3-nitrophthalic anhydride,-   3,6-difluorophthalic anhydride,-   3,6-dichlorophthalic anhydride,-   4,5-dichlorophthalic anhydride,-   3,4,5,6-tetrafluorophthalic anhydride,-   3,4,5,6-tetrachlorophthalic anhydride,-   3-methanesulfonyloxyphthalic anhydride.

Among the above-mentioned examples, 3-methanesulfonyloxyphthalicanhydride can be easily obtained from 3-hydroxyphthalic anhydride andmethanesulfonyl chloride according to the process described inTetrahedron Lett., 1988, 29, 5595-5598.

Similarly the compounds of the aforementioned formula (III), in which R³represents a hydrogen atom, starting materials for the compounds of theformula (IV), can be easily obtained, as described in the aforementionedpreparation process (a), by a catalytic hydrogen reduction of thecompounds represented by the aforementioned formula (IX) having a nitrogroup in place of an amino group, corresponding to the amino group(R³=H) in the formula (III).

The catalytic hydrogen reduction can be conducted in an adequate diluentand as examples of the diluent used in that case there can be mentionedethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether,butyl ether, dioxane, tetrahydrofuran (THF); alcohols, for example,methanol, ethanol, isopropanol, butanol, ethylene glycol, and ascatalytic reduction catalyst there can be mentioned palladium carbon,Raney nickel, platinum oxide.

It can be conducted at the temperatures generally between about 0 toabout 100° C., preferably room temperature to about 80° C.

Said reaction can be operated under normal pressure to elevatedpressure.

For example, an objective compound of the formula (III), in which R³represents hydrogen, can be obtained by hydrogenation of 1 mole of thenitro compound in a diluent, for example, ethanol in the presence of0.1-10% (w/w) palladium carbon.

Moreover, the compounds of the formula (E), in which R³ representshydrogen, can also be obtained by a reaction with a metal etc. insteadof a catalytic hydrogen reduction.

As a process using a metal etc. there can be mentioned, for example, aprocess of treating iron powder in acetic acid, a process of reactingzinc dust under the neutral condition (Organic Syntheses Collective Vol.II, p. 447), a process of reacting stannic chloride under an acidiccondition (Organic Syntheses Collective Vol. II, p. 254), a process ofreacting titanium trichloride under the neutral condition, etc.

As specific examples of the compounds of the formula (M), in which R³represents a hydrogen atom, there can be mentioned, for example,

-   1-(4-amino-3-methyl-benzyl)-1H-pyrazole,-   1-(4-amino-3-methyl-benzyl)-3-methyl-1H-pyrazole,-   1-(4-amino-3-methyl-benzyl)-4-methyl-1H-pyrazole,-   1-(4-amino-3-methyl-benzyl)-4,5-dichloro-1H-imidazole,-   1-(4-amino-3-methyl-benzyl)-1H-1,2,3-triazole,-   1-(4-amino-3-methyl-benzyl)-1H-1,2,4-triazole,-   1-(4-amino-3-methyl-benzyl-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-methyl-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(2-chloro-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(3-trifluoromethyl-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(4-trifluoromethyl-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(3,5-bis-trifluoromethyl-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-5-(3-trifluoromethoxy-phenyl)-1H-tetrazole,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolydin-2-one,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-1,3-dihydro-imidazol-2-one,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolydin-2,4-dione,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolydin-2,4,5-trione,-   1-(4-amino-3-methyl-benzyl)-3-(4-trifluoromethyl-phenyl)-1H-pyrazole,-   4-(4-amino-3-methyl-benzyl)-2-(2-fluoro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(2-chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-e-methyl-benzyl)-2-(2-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(3-fluoro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(3-chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(3-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-fluoro-phenyl)-4-(4-amino-3-methyl-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(4-chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(3,4-bis-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-2-(3,5-bis-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(4-amino-3-methyl-benzyl)-5-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)(2-chloro-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)-4-methyl-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)-4-(2-chloro-phenyl)-5-methylsulfanyl-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-amino-3-methyl-benzyl)-5-methylsulfanyl-4,4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   1-(4-amino-3-methyl-benzyl)-4-methyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-ethyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-propyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-isobutyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,2,2-trifluoro-ethyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4,4,4-trifluoro-butyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)    (3,3,3-trichloro-2-methyl-propyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)cyclopropyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-cyclohexyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-phenyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-benzyl)-4-(2-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(4-amino-3-methyl-phenyl)-ethyl]-4-(2-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl-4-(2-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-methoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-benzyl)-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-difluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-bromo-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-isopropyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-hydro-tetrazol-5-one,-   1-(4-amino-2-chloro-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-chloro-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-difluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethylsulfanyl-phenyl)-1,4-dihydro-tetrazo-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4′-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3′,5′-bis-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-bromo-2-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-fluoro-3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-bromo-4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-chloro-2-methoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-fluoro-3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2-fluoro-5-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-chloro-3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,4-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,4-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-fluoro-5-trifluoromethyl-phenyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,5-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,5-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-2-chloro-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-chloro-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-2-methoxy-benzyl)-4-(3,5-bis-fluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methoxy-benzyl)-4-(3,5-bis-trifluoromethyl-dihydro-tetrazol-5-one,-   1-(4-amino-3,5-dimethyl-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(4-amino-3-methyl-phenyl)ethyl]-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3-chloro-2-methoxy-5-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydrotetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,2,3-trifluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydrotetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,3,3-trifluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydrotetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(2,2,3,3,7-pentafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(3,5-chloro-2,6-diethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-benzyl-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-fluoro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-(4-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   -(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(2-fluoro-phenyl)ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(2-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(2-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(3-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(3-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(3-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(4-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(4-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(4-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(2,4-difluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(2,4-dichloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-amino-3-methyl-benzyl)-4-[1-(3,4-difluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one.

The compounds of the above-mentioned formula (IX) are novel compoundsand can be obtained, for example, by reacting compounds of the formula

wherein Y, m, A¹ and r have the same definition as aforementioned andM represents chloro, bromo or methylsulfonyloxy,and compounds of the formula

wherein Q, A², s and E have the same definition as aforementioned.

The compounds of the above-mentioned formula (XI) are compounds wellknown in the field of organic chemistry (cf. Chem. Abstr. 1963, 58,3444e; Bull. Soc. Chim. Fr. 1934, 539-545; J. Chem. Res. Miniprint,1987, 8, 2133-2139; J. Chem. Soc. B 1967, 1154-1158; J. Chem. Soc. 1961,221-222; J. Amer. Chem. Soc. 1989, 111, 5880-5886). Specifically therecan be mentioned as examples

-   4-nitrobenzyl chloride, (available on the market)-   4-bromobenzyl chloride, (available on the market)-   2-chloro-4-nitrobenzyl chloride,-   2-methyl-4-nitrobenzyl chloride,-   2-methoxy-4-nitrobenzyl chloride,-   3-chloro-4-nitrobenzyl chloride,-   3-methyl-4-nitrobenzyl chloride,-   3-methoxy-4-nitrobenzyl chloride,-   4-nitrobenzyl methanesulfonate,-   2-chloro-4-nitrobenzyl methanesulfonate,-   2-methyl-4-nitrobenzyl methanesulfonate,-   2-methoxy-4-nitrobenzyl methanesulfonate,-   3-chloro-4-nitrobenzyl methanesulfonate,-   3-methyl-4-nitrobenzyl methanesulfonate,-   3-methoxy-4-nitrobenzyl methanesulfonate,-   1-(3-chloro-4-nitro-phenyl)-ethyl methanesulfonate,-   1-(3-methyl-4-nitro-phenyl)-ethyl methanesulfonate,-   1-(3-methoxy-4-nitro-phenyl)-ethyl methanesulfonate.

The nitro-substituted benzoic acids and their esters, starting materialsfor the compounds of the formula (XI) are known from the literature(cf., for example, Chem. Ber. 1919, 52, 1083; Bull. Soc. Chim. Fr. 1962,2255-2261; Tetrahedron 1985, 115-118; Chem. Pharm. Bull., 1993, 41,894-906).

The compounds of the above-mentioned formula (XII) include knowncompounds and as their specific examples there can be mentioned,

-   1H-pyrrole,-   3-methyl-1H-pyrrole,-   2,5-dimethyl-1H-pyrrole,-   1H-pyrazole,-   3-methyl-1H-pyrazole,-   4-methyl-1H-pyrazole,-   4-chloro-1H-pyrazole,-   3,5-dimethyl-1H-pyrazole,-   1H-imidazole,-   4-methyl-1H-imidazole,-   4,5-dichloro-1H-imidazole,-   1H-[1,2,3]-triazole,-   1H-[1,2,4]-triazole,-   1H-tetrazole,-   5-methyl-1H-tetrazole,-   5-phenyl-1H-tetrazole,-   5-(2-chloro-phenyl)-1H-tetrazole,-   5-(4-chloro-phenyl)-1H-tetrazole,-   5-(3-trifluoromethyl-phenyl)-1H-tetrazole,-   5-(4-trifluoromethyl-phenyl)-1H-tetrazole,-   5-(3,5-bis-trifluoromethyl-phenyl)-1H-tetrazole,-   5-(3-trifluoromethoxy-phenyl)-1H-tetrazole,-   succinimide,-   1-(4-trifluoromethyl-phenyl)-imidazolidin-2-one-   1-(4-trifluoromethyl-phenyl)-1,3-dihydro-imidazol-2-one,-   3-(4-trifluoromethyl-phenyl)-imidazolidin-2,4-dione-   2-(2-chloro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   2-(2-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   2-(3-fluoro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   2-(3-chloro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   2-(3-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   2-(4-fluoro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   2-(4-chloro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   2-(4-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   2-(3,4-bis-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   2-(3,5-bis-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   5-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   4-(2-chloro-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   4-(4-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   5-methyl-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   4-(2-chloro-phenyl)-5-methylsulfanyl-2,4-dihydro-[1,2,4]triazol-3-one,-   5-methylsulfanyl-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-[1,2,4]triazol-3-one,-   1-methyl-1,4-dihydro-tetrazol-5-one,-   1-ethyl-1,4-dihydro-tetrazol-5-one,-   1-propyl-1,4-dihydro-tetrazol-5-one,-   1-isobutyl-1,4-dihydro-tetrazol-5-one,-   1-(2,2,2-trifluoro-ethyl) 1,4-dihydro-tetrazol-5-one,-   1-(4,4,4-trifluoro-butyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,3,3-trichloro-2-methyl-propyl)-1,4-dihydro-tetrazol-5-one,-   1-cyclopropyl-1,4-dihydro-tetrazol-5-one,-   1-cyclohexyl-1,4-dihydro-tetrazol-5-one,-   1-phenyl-1,4-dihydro-tetrazol-5-one,-   1-(2-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-methoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-fluoro-phenyl)-1,4-dihydro-tetrazol-5′-one,-   1-(3-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-difluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-fluoro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-chloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-bromo-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-isopropyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4′-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-trifluoromethylsulfanyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4′-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one,-   1-(3′,5′-bis-trifluoromethyl-biphenylyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-bromo-2-fluoro-phenyl-1,4-dihydro-tetrazol-5-one,-   1-(2-fluoro-3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-bromo-4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-chloro-4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-fluoro-3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-fluoro-5-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-chloro-3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,4-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,4-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,4-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-fluoro-5-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-dichloro-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-dimethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-chloro-2-methoxy-5-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-1,4-dihydro-tetrazol-5-one,-   1-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydro-tetrazol-5-one,-   1-(2,2,3-trifluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydro-tetrazol-5-one,-   1-(2,3,3-trifluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydro-tetrazol-5-one,-   1-(2,2,3,3,7-pentafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-dichloro-2,6-diethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-thiophen-2-yl-1,4-dihydro-tetrazol-5-one,-   1-benzyl-1,4-dihydro-tetrazol-5-one,-   1-(4-fluoro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-chloro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-trifluoromethyl-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(2-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(2-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(2-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(3-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(3-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(3-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(4-fluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(4-chloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(4-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(2,4-difluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(2,4-dichloro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(3,4-difluoro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one.

Furthermore, there can be provided from the processes described in theliterature, for example,1-(4-trifluoromethyl-phenyl)imidazolidin-2,4,5-trione from4-trifluoromethylphenylurea (cf. J. Chem. Soc. Perkin Trans. 2, 1977,934, according to the process described in Chem. Ber. 1907, 40, 3737),there can be provided 3-(4-trifluoromethyl-phenyl)-1H-pyrazole from4-trifluoromethylacetophenone, available on the market (cf. Synthesis2001, 55-62), and further there can be provided2-phenyl-2,4-dihydro-1,2,4-triazol-3-one and2-(2-fluorophenyl)-2,4-dihydro-1,2,4-triazol-3-one (cf. J. Prakt. Chem.1907, 75, 131), and furthermore, there can be provided 1-mono-(ordi-)(trifluoromethyl)phenyl-1,4-dihydro-tetrazol-5-one by a reaction ofmono-(or di-)(trifluoromethyl)phenyl isocyanate and known trimethylsilylazide (cf. EP-A 0 146 279, Chem. Pharm. Bull., 1996, 44,314-327).

The process to prepare the compounds of the above-mentioned formula (In)can be conducted in an adequate diluent. As examples of the diluent usedin that case there can be mentioned aliphatic, alicyclic and aromatichydrocarbons (may be optionally chlorinated), for example, pentane,hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene,xylene, dichloromethane; ethers, for example, ethyl ether, methyl ethylether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME),tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM); ketones,for example, acetone, methyl ethyl ketone (MEK), methyl isopropylketone, methyl isobutyl ketone (MIBK); nitrites, for example,acetonitrile, propionitrile, acrylonitrile; esters, for example, ethylacetate, amyl acetate; acid amides, for example, dimethylformamide(DMF), dimethylacetamide (DMA), N-methylpyrrolidone,1,3-dimethyl-2-imidazolidinone, hexamethyl phosphoric triamide (HMPA).

The reaction can be conducted in the presence of an acid binder and assuch an acid binder there can be mentioned, as inorganic base, hydrides,hydroxides, carbonates, bicarbonates, etc. of alkali metals and alkalineearth metals, for example, sodium hydride, lithium hydride, sodiumhydrogen carbonate, potassium hydrogen carbonate, sodium carbonate,potassium carbonate, lithium hydroxide, sodium hydroxide, potassiumhydroxide, calcium hydroxide; inorganic alkali metal, amides, forexample, lithium amide, sodium amide, potassium amide; as organic base,alcoholates, tertiary amines, dialkylaminoanilines and pyridines, forexample, triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA),N,N-dimethylaniline, N,N-diethylaniline, pyridine,4-dimethylaminopyridine (DMAP), 1,4-diazabicyclo[2.2.2]octane (DABCO)and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

The reaction can also be conducted by a process using a phase-transfercatalyst. As examples of the diluent used in that case there can bementioned water; aliphatic, alicyclic and aromatic hydrocarbons (may beoptionally chlorinated), for example, pentane, hexane, cyclohexane,petroleum ether, ligroine, benzene, toluene, xylene; ethers, forexample, ethyl ether, methyl ethyl ether, iso-propyl ether, butyl ether,dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycoldimethyl ether (DGM).

As examples of phase-transfer catalyst there can be mentioned,quaternary ions, for example, tetramethylammonium bromide,tetrapropylammonium bromide, tetrabutylammonium bromide,tetrabutylammonium bissulfate, tetrabutylammonium iodide,trioctylmethylammonium chloride, benzyltriethylammonium bromide,butylpyridinium bromide, heptylpyridinium bromide,benzyltriethylammonium chloride; crown ethers, for example,dibenzo-18-crown-6, dicyclohexyl-18-crown-6, 18-crown-6; cryptands, forexample, [2.2.2]-cryptate, [2.1.1]-cryptate, [2.2.1]-cryptate,[2.2.B]-cryptate, [2O2O2S]-cryptate, [3.2.2]-cryptate.

The reaction can be conducted in a substantially wide range oftemperature. It can be conducted at the temperatures in a range ofgenerally about 0° C. to about 200° C., preferably room temperature toabout 150° C. Although said reaction is conducted desirably under normalpressure, it can be operated also under elevated pressure or underreduced pressure.

In conducting the reaction, the aimed compounds can be obtained, forexample, by reacting 1 mole amount to a little excess amount of acompound of the formula (XII) to 1 mole of the compounds of the formula(XI) in a diluent, for example, DMF, in the presence of potassiumcarbonate.

As specific examples of the compounds of the aforementioned formula(IX), obtained according to the above-mentioned process, there can bementioned, for example,

-   1-(4-nitro-benzyl)-1H-pyrrole,-   1-(3-methyl-4-nitro-benzyl)-1H-pyrazole,-   3-methyl-1-(3-methyl-4-nitro-benzyl)-1H-pyrazole,-   4-methyl-1-(3-methyl-nitro-benzyl)-1H-pyrazole,-   4,5-dichloro-1-(3-methyl-4-nitro-benzyl)-1H-imidazole,-   1-(3-methyl-4-nitro-benzyl)-1H-1,2,3-triazole,-   1-(3-methyl-4-nitro-benzyl)-H-1,2,4-triazole,-   1-(3-methyl-4-nitro-benzyl)-1H-tetrazole,-   5-methyl-1-(3-methyl-4-nitro-benzyl)-1-H-tetrazole,-   5-(2-chloro-phenyl)-1-(3-methyl-4-nitro-benzyl)-1H-tetrazole,-   5-(3-trifluoromethyl-phenyl)-1-(3-methyl-4-nitro-benzyl)-1H-tetrazole,-   5-(4-trifluoromethyl-phenyl)-1-(3-methyl-4-nitro-benzyl)-1H-tetrazole,-   5-(3,5-bis-trifluoromethyl-phenyl)-1-(3-methyl-4-nitro-benzyl)-1H-tetrazole,-   5-(3-trifluoromethoxy-phenyl)-1-(3-methyl-4-nitro-benzyl)-1H-tetrazole,-   1-(3-methyl-4-nitro-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolidin-2-one,-   1-(3-methyl-4-nitro-benzyl)-3-(4-trifluoromethyl-phenyl)-1,3-dihydro-imidazol-2-one,-   1-(3-methyl-4-nitro-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolidin-2,4-dione,-   1-(3-methyl-4-nitro-benzyl)-3-(4-trifluoromethyl-phenyl)-imidazolidin-2,4,5-trione,-   1-(3-methyl-4-nitro-benzyl)-3-(4-trifluoromethyl-phenyl)-1H-pyrazole,-   2-(2-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(2-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(3-methyl-4-nitro-benzyl)-2-(2-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(3-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(3-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(3-methyl-4-nitro-benzyl)-2-(3-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(4-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(3-methyl-4-nitro-benzyl)-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(3,4-bis-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(3,5-bis-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(3-methyl-4-nitro-benzyl)-5-trifluoromethyl-2-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(2-chloro-phenyl)-2-(3-methyl-4-nitro-benzyl)-2,4-dihydro-1,2,4-triazol-3-one,-   2-(3-methyl-4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   5-methyl-2-(3-methyl-4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   4-(2-chloro-phenyl)-2-(3-methyl-4-nitro-benzyl)-5-methylsulfanyl-2,4-dihydro-1,2,4-triazol-3-one,-   2-(3-methyl-4-nitro-benzyl)-5-methylsulfanyl-4-(4-trifluoromethyl-phenyl)-2,4-dihydro-1,2,4-triazol-3-one,-   1-methyl-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-ethyl-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-propyl-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-isobutyl-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(2,2,2-trifluoro-ethyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(4,4,4-trifluoro-butyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(3,3,3-trichloro-2-methyl-propyl)-1,4-dihydro-tetrazol-5-one,-   1-cyclopropyl-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-cyclohexyl-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-phenyl-1,4-dihydro-tetrazol-5-one,-   1-(2-fluoro-phenyl)(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-chloro-phenyl)-4-(4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-chloro-phenyl)-4-[1-(3-methyl-4-nitro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(2-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(2-methoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(2-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(3-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-difluoromethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-bromo-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(4-methyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-isopropyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-chloro-4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-chloro-4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   -1-(3-methyl-4-nitro-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-difluoromethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-nitro-benzyl)-4-(4-trifluoromethoxy-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(4-trifluoromethylsulfanyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(4′-trifluoromethyl-biphenyl-4-yl)-1,4-dihydro-tetrazol-5-one,-   1-(3′,5′-bis-trifluoromethyl-biphenyl-4-yl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-bromo-2-fluoro-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-fluoro-3-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-bromo-4-trifluoromethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   -(3-chloro-4-trifluoromethoxy-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-fluoro-3-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-fluoro-5-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-chloro-3-fluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,4-chloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,4-bis-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-fluoro-5-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-dichloro-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-dimethoxy-phenyl)    (3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-bis-trifluoromethyl-phenyl)-4-(2-chloro-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-bis-trifluoromethyl-phenyl)-4-(3-chloro-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-bis-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-bis-trifluoromethyl-phenyl)-4-(2-methoxy-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-bis-trifluoromethyl-phenyl)-4-(3-methoxy-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-bis-trifluoromethyl-phenyl)-4-(3,5-dimethyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-bis-trifluoromethyl-phenyl)-4-[1-(3-methyl-4-nitro-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-(3-chloro-2-methoxy-5-methyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(2,2-difluoro-benzo[1,3]dioxol-5-yl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(2,2,3,3-tetrafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydrotetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)(2,2,3-trifluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydrotetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(2,3,3-trifluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydrotetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(2,2,3,3,7-pentafluoro-2,3-dihydro-benzo[1,4]dioxin-6-yl)-1,4-dihydro-tetrazol-5-one,-   1-(3,5-dichloro-2,6-diethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-benzyl-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-fluoro-benzyl)(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(4-chloro-benzyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-(4-trifluoromethyl-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(2-fluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(2-chloro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-[1-(2-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(3-fluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(3-chloro-phenyl)ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-[1-(3-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(4-fluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(4-chloro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-(3-methyl-4-nitro-benzyl)-4-[1-(4-trifluoromethyl-phenyl)-ethyl]-1,4-dihydro-tetrazol-5-one,-   1-[1-(2,4-difluoro-phenyl)-ethyl](3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(2,4-dichloro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,-   1-[1-(3,4-difluoro-phenyl)-ethyl]-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one.

And as specific examples of the compounds of the formula (IV), startingmaterials in the preparation process (b), there can be mentioned, forexample,

-   2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-fluoro-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-chloro-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-bromo-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-iodo-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4,7-dichloro-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   5,6-dichloro-2-{2-methyl-4-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-nitro-2-{2-methyl-4-[5-oxo(2-chloro-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-methyl-2-{2-methyl-[5-oxo-4-(2-chloro-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-fluoro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-chloro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-bromo-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-iodo-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4,7-dichloro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   5,6-dichloro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-nitro-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-methyl-2-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl)-isoindol-1,3-dione,-   2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-fluoro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-chloro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-bromo-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-iodo-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4,7-dichloro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   5,6-dichloro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-nitro-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione,-   4-methyl-2-{2-methyl-4-[5-oxo-4-(3,5-bis-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-isoindol-1,3-dione.

The compounds of the formula (V), starting materials in the preparationprocess (b), are either well-known compounds in the field of organicchemistry or can be synthesized according to the process described inDE-A 20 45 905, WO 01/23350 etc. As their specific examples there can bementioned ethylamine, diethylamine, n-propylamine, isopropylamine,n-butylamine, sec-butylamine, isobutylamine, t-butylamine, t-amylamine,cyclopropylamine, cyclopentylamine, cyclohexylamine,3-methylcyclohexylamine, 2-(methylthio)-ethylamine,2-(ethylthio)-ethylamine, 1-methyl-2-(methylthio) ethylamine,1,1-dimethyl-2-(methylthio)-ethylamine, etc.

Compounds of the formula (VI), starting materials in the preparationprocess (c), include known compounds or can be easily obtained accordingto the process described in EP-A 0 919 542, EP-A 1 006 107 etc. and astheir specific examples there can be mentioned,

-   N-isopropyl-phthalamic acid,-   3-fluoro-N-isopropyl-phthalamic acid,-   3-chloro-N-isopropyl-phthalamic acid,-   3-bromo-N-isopropyl-phthalamic acid,-   3-iodo-N-isopropyl-phthalamic acid,-   N-isopropyl-3-nitro-phthalamic acid,-   N-(1-methyl-2-methylsulfanil-ethyl)-phthalamic acid,-   3-fluoro-N-(1-methyl-2-methylsulfanil-ethyl)-phthalamic acid,-   3-chloro-N-(1-methyl-2-methylsulfanil-ethyl)-phthalamic acid,-   3-bromo-N-(1-methyl-2-methylsulfanil-ethyl)-phthalamic acid,-   3-iodo-N-(1-methyl-2-methylsulfanil-ethyl)-phthalamic acid,-   N-(1-methyl-2-methylsulfanil-ethyl)-3-nitro-phthalamic acid,-   N-(1,1-dimethyl-2-methylsulfanil-ethyl)-phthalamic acid,-   N-(1,1-dimethyl-2-methylsulfanil-ethyl)-3-fluoro-phthalamic acid,-   3-chloro-N-(1,1-dimethyl-2-methylsulfanil-ethyl)-phthalamic acid,-   3-bromo-N-(1,1-dimethyl-2-methylsulfanil-ethyl)-phthalamic acid,-   N-(1,1-dimethyl-2-methylsulfanil-ethyl)-3-iodo-phthalamic acid,-   N-(1,1-dimethyl-2-methylsulfanil-ethyl)-3-nitro-phthalamic acid,-   N-isopropyl-3-methanesulfonyloxy-phthalamic acid,-   N-(1-methyl-2-methylsulfanil-ethyl)-3-methanesulfonyloxy-phthalamic    acid,-   N-(1,1-dimethyl-2-methylsulfanil-ethyl)-3-methanesulfonyloxy-phthalamic    acid.

The compounds of the above-mentioned formula (VI) can be easily obtainedgenerally by reacting phthalic anhydrides of the formula

wherein X and n have the same definition as aforementioned,and amines of the formula

wherein R¹ and R² have the same definition as aforementioned.

The above-mentioned compounds of the formula (XII) and the compounds ofthe formula (XIV) are all well-known in the field of organic chemistryand specifically there can be mentioned the following as examples.

As examples of the compounds of the formula (XM) there can be mentioned,

phthalic anhydride, 3-fluorophthalic anhydride, 3-chlorophthalicanhydride, 3-bromophthalic anhydride, 3-iodophthalic anhydride,3-methylphthalic anhydride, 3-nitrophthalic anhydride,3,6-difluorophthalic anhydride, 3,6-dichlorophthalic anhydride,4,5-dichlorophthalic anhydride, 3,4,5,6-tetrafluorophthalic anhydride,3,4,5,6-tetrachlorophthalic anhydride, 3-methanesulfonyloxyphthalicanhydride.

As examples of the compounds of the formula (XIV) there can bementioned,

ethylamine, n-propylamine, isopropylamine, n-butylamine, sec-butylamine,isobutylamine, t-butylamine, t-amylamine, cyclopropylamine,cyclopentylamine, cyclohexylamine, 2-(methylthio)-ethylamine,2-(ethylthio)-ethylamine, 1-methyl-2-(methylthio)-ethylamine,1,1-dimethyl-2-(methylthio)ethylamine.

These amines can be easily obtained also by the process described inDE-A 20 45 905, WO 01/23350.

The reaction for synthesizing the compounds of the formula (VI) can beconducted according to the process described in J. Org. Chem. 1981, 46,175 etc.

Such a reaction can be conducted in an adequate diluent and as examplesof the diluent used in that case there can be mentioned aliphatic,alicyclic and aromatic hydrocarbons (may be optionally chlorinated), forexample, pentane, hexane, cyclohexane, petroleum ether, ligroine,benzene, toluene, xylene, dichloromethane, chloroform, carbontetrachloride, 1,2-dichloroethane, chlorobenzene, dichlorobenzene;ethers, for example, ethyl ether, methyl ethyl ether, isopropyl ether,butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF),diethylene glycol dimethyl ether (DGM); ketones, for example, acetone,methyl ethyl ketone (MEK), methyl isopropyl ketone, methyl isobutylketone (MIBK), etc.; nitrites, for example, acetonitrile, propionitrile,acrylonitrile; esters, for example, ethyl acetate, amyl acetate.

The preparation process (e) can be conducted in the presence of a baseand as such a base there can be mentioned tertiary amines,dialkylaminoanilines and pyridines, for example, triethylamine,1,1,4,4-tetramethylethylenediamine (TMEDA), N,N-dimethylaniline,N,N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP),1,4-diazabicyclo[2.2.2]octane (DABCO) and1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), etc.

The reaction can be conducted in a substantially wide range oftemperature. It can be conducted at the temperatures in a range ofgenerally about −70° C. to about 100° C., preferably about 50° C. toabout 80° C. Although said reaction is conducted desirably under normalpressure, it can be operated also under elevated pressure or underreduced pressure.

In conducting the reaction, the aimed compounds can be obtained, forexample, by reacting 1 mole amount to 4 mole amount of the compounds ofthe formula (XIV) to 1 mole of the compounds of the formula X in adiluent, for example, acetonitrile.

The compounds of the formula (VII), starting materials in thepreparation process (d), are novel compounds and can be easily obtained,for example, by reacting a compound represented by the formula (VIII-a)

wherein X, n, A¹, r, Q, A², s and E have the same definition asaforementioned, in the presence of a condensing agent (cf. e.g. J. Med.Chem. 1967, 10, 982).

The compounds of the above-mentioned formula (VIII-a) are also novelcompounds and can be easily obtained by reacting phthalic anhydrides ofthe aforementioned formula (X) and the compounds of the aforementionedformula (III), in which R³ is a hydrogen atom.

The above-mentioned reaction of a compound of the formula (VIII-a) and acompound of the formula (III), in which R³ is a hydrogen atom, can beconducted in an adequate diluent and as examples of the diluent used inthat case there can be mentioned aliphatic, alicyclic and aromatichydrocarbons (may be optionally chlorinated), for example, pentane,hexane, cyclohexane, petroleum ether, ligroine, benzene, toluene,xylene, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example,ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane,dimethoxyethane (DME), tetrahydrofuran (THF), diethylene glycol dimethylether (GM); ketones, for example, acetone, methyl ethyl ketone (MEK),methyl isopropyl ketone, methyl isobutyl ketone (MIBK); nitriles, forexample, acetonitrile, propionitrile, acrylonitrile, etc.; esters, forexample, ethyl acetate, amyl acetate.

The reaction can be conducted in the presence of a base and as such abase there can be mentioned tertiary amines, dialkylaminoanilines andpyridines, for example, triethylamine,1,1,4,4-tetramethylethylenediamine (TMEDA), N,N-dimethylaniline,N,N-diethylaniline, pyridine, 4-dimethylaminopyridine (DMAP),1,4-diazabicyclo[2.2.2]octane (DABCO) and1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

The reaction can be conducted in a substantially wide range oftemperature. It can be conducted at the temperatures in a range ofgenerally about −70° C. to about 100° C., preferably about −50° C. toabout 80° C.

Although said reaction is conducted desirably under normal pressure, itcan be operated also under elevated pressure or under reduced pressure.

In conducting the reaction, the aimed compounds can be obtained, forexample, by reacting 1 mole amount to 4 mole amount of the compounds ofthe formula (III), in which R³ is a hydrogen atom, to 1 mole of thecompounds of the formula (X) in a diluent, for example, acetonitrile.

As specific examples of the compounds of the above-mentioned formula(OM-a), there can be mentioned, for example,

-   N-{4-[4-(2-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-ylmethyl]-2-methyl-phenyl}-6-iodo-phthalamic    acid,-   6-iodo-N-{2-methyl-4-[5-oxo-4-(2-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-phthalamic    acid,-   N-{4-[4-(4-fluoro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-ylmethyl]-2-methyl-phenyl}-6-iodo-phthalamic    acid,-   N-{4-[4-(4-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-ylmethyl]-2-methyl-phenyl}-6-iodo-phthalamic    acid,-   6-iodo-N-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-phthalamic    acid, etc.

And as specific examples of the compounds of the above-mentioned formula(VII), there can be mentioned, for example,

-   1-(2-chloro-phenyl)-4-[4-(4-iodo-3-oxo-3H-isobenzofuran-1,4-ylideneamino)-3-methyl-benzyl]-1,4-dihydro-tetrazol-5-one,-   1-[4-(4-iodo-3-oxo-3H-isobenzofuran-1-ylideneamino)-3-methyl-benzyl]-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,-   1-(2-fluoro-phenyl)-4-[4-(4-iodo-3-oxo-3H-isobenzofuran-4-ylideneamino)-3-methyl-benzyl]-1,4-dihydro-tetrazol-5-one,-   1-(4-chloro-phenyl)-4-[4-(4-iodo-3-oxo-3H-isobenzofuran-1-ylideneamino)-3-methyl-benzyl]-1,4-dihydro-tetrazol-5-one,-   1-[4-(4-iodo-3-oxo-3H-isobenzofuran-1-ylideneamino)-3-methyl-benzyl]4-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,    etc.

The compounds of the formula (V), also starting materials in thepreparation process (d), have been described in the aforementionedpreparation process (b).

The compounds of the formula (VIII), starting materials in thepreparation process (e), are novel compounds and can be easily obtained,as described in the aforementioned preparation process (d), generally byreacting phthalic anhydrides of the aforementioned formula (Q with thecompounds of the aforementioned formula (III).

The reaction is the same as already described in the aforementionedpreparation process (d).

As specific examples of the compounds of the formula (VM) there can bementioned,

-   N-{4-[4-(2-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-ylmethyl]-2-methyl-phenyl}-N-methyl-6-iodo-phthalamic    acid,-   6-iodo-N-{2-methyl-4-[5-oxo-4-(2-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-phenyl}-N-methyl-phthalamic    acid,-   N-{4-[4-(4-fluoro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-ylmethyl]-2-methyl-phenyl}-N-methyl-6-iodo-phthalamic    acid,-   N-{4-[4-(4-chloro-phenyl)-5-oxo-4,5-dihydro-tetrazol-1-ylmethyl]-2-methyl-phenyl}-N-methyl-6-iodo-phthalamic    acid,-   6-iodo-N-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-tetrazol-1-ylmethyl]-N-methyl-phenyl}-phthalamic    acid.

The compounds of the formula (V), also starting materials in thepreparation process (e), are identical with those in the aforementionedpreparation processes (b) and (d).

As another preparation process for the compounds of the aforementionedformula (VIII), the common starting materials in the preparation process(d) and preparation process (e), in which X and Y represent other groupsthan bromo or iodo, compounds of the formula

wherein n, R³, m, A¹, r, Q, A², s and E have the same definition asaforementioned, and X¹ and Y¹ each has a definition of theaforementioned X and Y but excluding bromo and iodo, is reacted with ametal reagent, for example, butyl lithium, and then reacted with carbondioxide to obtain the compounds of the corresponding formula (VIII)(however, X and Y do not represent bromo or iodo).

The compounds of the above-mentioned formula (XV) are novel compoundsand can be easily obtained generally by reacting a benzoic acid haliderepresented by the formula

wherein X¹ and n have the same definition as aforementioned, andHal represents a halogen atom,with the compounds of the aforementioned formula (I)

wherein R³, Y, m, A¹, r, Q, A², s and E have the same definition asaforementioned.

The compounds of the above-mentioned formula (XVI are well-knowncompounds in the field of organic chemistry and there can be mentionedspecifically,

benzoyl chloride, 3-fluorobenzoyl chloride, 3-chlorobenzoyl chloride,3-methylbenzoyl chloride, 3-nitrobenzoyl chloride.

The reaction to prepare the compounds of the above-mentioned formula(XV) can be conducted in an adequate diluent and as examples of thediluent used in that case there can be mentioned aliphatic, alicyclicand aromatic hydrocarbons (may be optionally chlorinated), for example,pentane, hexane, cyclohexane, petroleum ether, ligroine, benzene,toluene, xylene, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane, chlorobenzene, dichlorobenzene; ethers, for example,ethyl ether, methyl ethyl ether, isopropyl ether, butyl ether, dioxane,dimethoxyethane (DME), tetrahydrofuran (THF); diethylene glycol dimethylether (DGM); esters, for example, ethyl acetate, amyl acetate.

The reaction can be conducted in the presence of an acid binder and assuch an acid binder there can be mentioned, as inorganic base,hydroxides, carbonates, bicarbonates, etc. of alkali metals and alkalineearth metals, for example, sodium hydrogen carbonate, potassium hydrogencarbonate, sodium carbonate, potassium carbonate, lithium hydroxide,sodium hydroxide, potassium hydroxide, calcium hydroxide; as organicbase, alcoholates, tertiary amines, dialkylaminoanilines and pyridines,for example, triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA),N,N-dimethylaniline, N,N-diethylaniline, pyridine,4-dimethylaminopyridine (DMAP), 1,4-diazabicyclo[2.2.2]octane (DABCO)and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).

The reaction can be conducted in a substantially wide range oftemperature. It can be conducted at the temperatures in a range ofgenerally about −20 to about 150° C., preferably about 0° C. to about100° C.

Although said reaction is conducted desirably under normal pressure, itcan be operated also under elevated pressure or under reduced pressure.

In conducting the reaction, the aimed compounds can be obtained, forexample, by reacting 1 mole amount to a little excess amount of thecompounds of the formula (III) to 1 mole of the compounds of the formula(XVI) in a diluent, for example, 1,2-dichloroethane, in the presence oftriethylamine.

The compounds of the formula (I), starting materials in the preparationprocess (f), are the compounds included in the aforementioned formula(I) of the present invention. By oxidizing C₁-C₆-alkylthio-C₁-C₆-alkyl,the definition of R^(1f) in the formula (If), compounds of the formula(I) corresponding to C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl orC₁-C₆-alkylsulfonyl-C₁-C₆-alkyl can be obtained.

The compounds of the formula (If) can be prepared by the aforementionedpreparation processes (a), (b), (c), (d) and/or (e).

As specific examples of the compounds of the formula (If) there can bementioned, for example,

-   3-iodo-N²-(1-methyl-2-methylsulfanyl-ethyl)-N¹-{2-methyl-4-[5-oxo-4-(3-trifluoromethyl-phenyl)-4,5-dihydro-triazol-1-ylmethyl]-phenyl}-phthalamide,-   N²-(1,1-dimethyl-2-methylsulfanyl-ethyl)-3-iodo-N¹-{2-methyl-4-[5-oxo-4-(3-trifluoromethylphenyl)-4,5-dihydro-triazol-1-ylmethyl]-phenyl}-phthalamide,-   3-iodo-N²-(1-methyl-2-methylsulfanyl-ethyl)-N′-{2-methyl-4-[5-oxo-4-(4-trifluoromethyl-phenyl)-4,5-dihydro-triazol-1-ylmethyl]-phenyl}-phthalamide,-   N²-(1,1-dimethyl-2-methylsulfanyl-ethyl)-3-iodo-N′-{2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydro-triazol-1-ylmethyl]-phenyl}-phthalamide,-   N¹-{4-[4-(3,5-bis-trifluoromethyl-phenyl)-5-oxo-4,5-dihydro-triazol-1-ylmethyl]-2-methyl-phenyl}-3-iodo-N²-(1-methyl-2-methylsulfanyl-ethyl)-phthalamide,-   N¹-(4-[4-(3,5-bis-trifluoromethyl-phenyl)₅-oxo(4,5-dihydro-triazol-1-ylmethyl]-2-methyl-phenyl}-N²-(1,1-dimethyl-2-methylsulfanyl-ethyl)-3-iodo-phthalamide,    etc.

The reaction of the aforementioned preparation process (a) can beconducted by using adequate diluents, singly or mixed, and as examplesof the diluents used in that case there can be mentioned water;aliphatic, alicyclic and aromatic hydrocarbons (may be optionallychlorinated), for example, pentane, hexane, cyclohexane, petroleumether, ligroine, benzene, toluene, xylene, dichloromethane, chloroform,carbon tetrachloride, 1,2-dichloroethane, chlorobenzene,dichlorobenzene; ethers, for example, ethyl ether, methyl ethyl ether,isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME),tetrahydrofuran (THF), diethylene glycol dimethyl ether (DGM); nitriles,for example, acetonitrile, propionitrile, acrylonitrile; esters, forexample, ethyl acetate, amyl acetate.

The preparation process (a) can be conducted in the presence of an acidcatalyst and as examples of such an acid catalyst there can be mentionedmineral acids, for example, hydrochloric acid, sulfuric acid, organicacids, for example, acetic acid, trifluoroacetic acid, propionic acid,methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid.

The preparation process (a) can be conducted in a substantially widerange of temperature. It can be conducted at the temperatures in a rangeof generally about −20° C. to about 100° C., preferably about 0° C. toabout 100° C.

Although said reaction is conducted desirably under normal pressure, itcan be operated also under elevated pressure or under reduced pressure.

In conducting the preparation process (a), the aimed compounds can beobtained, for example, by reacting 1 mole amount to a little excessamount of the compounds of the formula (III) to 1 mole of the compoundsof the formula (II) in a diluent, for example, 1,2-dichloroethane, inthe presence of 0.01-0.1 mole amount of p-toluenesulfonic acid.

The preparation process (b) can be conducted in the presence of a basesuch as tertiary amines, dialkylaminoanilines and pyridines, forexample, triethylamine, 1,1,4,4-tetramethylethylenediamine (TMEDA),N,N-dimethylaniline, N,N-diethylaniline, pyridine,4-dimethylaminopyridine (DMAP), 1,4-diazabicyclo[2.2.2]octane (DABCO)and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), etc.

The preparation process (b) can be conducted in a substantially widerange of temperature. It can be conducted at the temperatures in a rangeof generally about −20° C. to about 150° C., preferably room temperatureto about 100° C. Although said reaction is conducted desirably undernormal pressure, it can be operated also under elevated pressure orunder reduced pressure.

In conducting the preparation process (b), the aimed compounds can beobtained, for example, by reacting 1 mole amount to 25 mole amount ofthe compounds of the formula (V) to 1 mole of the compounds of theformula (IV).

The aforementioned preparation processes (c), (d) and (e) can beconducted under the similar conditions as for the above-mentionedpreparation process (a).

The reaction of the aforementioned preparation process (f) can beconducted in an adequate diluent and as examples of the diluents used inthat case there can be mentioned aliphatic, alicyclic and aromatichydrocarbons (may be optionally chlorinated), for example, benzene,toluene, xylene, dichloromethane, chloroform, carbon tetrachloride,1,2-dichloroethane, chlorobenzene, dichlorobenzene; alcohols, forexample, methanol, ethanol, isopropanol, butanol, acids: formic acid,acetic acid.

As oxidizing agent to be used there can be mentioned, for example,metachloroperbenzoic acid, peracetic acid, potassium metaperiodate,potassium hydrogen persulfate (oxone), hydrogen peroxide.

The preparation process (f) can be conducted in a substantially widerange of temperature. It can be conducted at the temperatures in a rangeof generally about −50° C. to about 150° C., preferably about −10° C. toabout 100° C.

Although said reaction is conducted desirably under normal pressure, itcan be operated also under elevated pressure or under reduced pressure.

In conducting the preparation process (f), the aimed compounds can beobtained, for example, by reacting 1 mole amount to 5 mole amount of anoxidizing agent to 1 mole of the compounds of the formula (If) in adiluent, for example, dichloromethane.

The reaction of the preparation process (f) can be conducted accordingto the process described in, for example, Jikken Kagaku Kohza (Lecturesof experimental chemistry), compiled by the Chemical Society of Japan,4^(th) ed., Vol. 24, page 350 (1992) published by Maruzen or ibid., page365.

The compounds of the formula (I) of the present invention show stronginsecticidal action. They can, therefore, be used as insecticidalagents. And the active compounds of the formula (I) of the presentinvention exhibit exact controlling effect against harmful insectswithout phytotoxicity against cultured plants. The compounds of thepresent invention can be used for controlling a wide variety of pests,for example, harmful sucking insects, biting insects and otherplant-parasitic pests, stored grain pests, hygienic pests, etc. andapplied for their extermination.

As examples of such pests there can be mentioned the following pests:

As insects, there can be mentioned coleoptera pests, for example,Callosobruchus Chinensis, Sitophilus zeamais, Tribolium castaneum,Epilachna vigintioctomaculata, Agriotes fuscicollis, Anomala rufocuprea,Leptinotarsa decemlineata, Diabrotica spp., Manochamus alternatus,Lissorhoptrus oryzophilus, Lyctus bruneus;

Lepidoptera pests, for example, Lymantria dispar, Malacosoma neustria,Pieris rapae, Spodoptera litura, Mamestra brassicae, Chilo suppressalis,Pyrausta nubilalis, Ephestia cautella, Adoxophyes orana, Carpocapsapomonella, Agrotis fucosa, Galleria mellonella, Plutella maculipennis,Heliothis virescens, Phyllocnistis citrella;

Heimiptera pests, for example, Nephotettix cincticeps, Nilaparvatalugens, Pseudococcus comstocki, Unaspis yanonensis, Myzus persicae,Aphis pomi, Aphis gossypii, Rhopalosiphum pseudobrassicas, Stephanitisnashi, Nazara spp., Cimex lectularius, Trialeurodes vaporariorum, Psyllaspp.;

Orthoptera pests, for example, Blatella germanica, Periplanetaamericana, Gryllotalpa africana, Locusta migratoria migratoriodes;

Homoptera pests, for example, Reticulitermes speratus, Coptotermesformosanus;

Diptera pests, for example, Musca domestica, Aedes aegypti, Hylemiaplatura, Culex pipiens, Anopheles slnensis, Culex tritaeniorhynchus.

Moreover, as mites there can be mentioned, for example, Tetranychustelarius, Tetraiychus urticae, Panonychus citri, Aculops pelekassi,Tarsonemus spp.

Furthermore, as nematodes there can be mentioned, for example,Meloidogyne incognita, Bursaphelenchus lignicolus Manmiya et Kiyohara,Aphelenchoides basseyi, Heterodera glycines, Pratylenchus spp.

In addition, in the field of veterinary medicine, the novel compounds ofthe present invention can be effectively used against various harmfulanimal-parasitic pests (endoparasites and ectoparasites), for example,insects and helminthes. As examples of such animal-parasitic pests therecan be mentioned the following pests:

As insects there can be mentioned, for example, Gastrophilus spp.,Stomoxys spp., Trichodectes spp., Rhodnius spp., Ctenocephalides canis.

As mites there can be mentioned, for example, Ornithodoros spp., Ixodesspp., Boophilus spp.

In the present invention substances having insecticidal action againstpests, which include all of them, are in some cases called asinsecticides.

The active compounds of the present invention can be made into customaryformulation forms, when they are used as insecticides. As formulationforms there can be mentioned, for example, solutions, emulsions,wettable powders, water dispersible granules, suspensions, powders,foaming agents, pastes, tablets, granules, aerosols, activecompound-impregnated natural and synthetic substances, microcapsules,seed coating agents, formulations used with burning equipment (asburning equipment, for example, fumigation and smoking cartridges, cans,coils, etc.), ULV [cold mist, warm mist], etc.

These formulations can be prepared according to per se known methods,for example, by mixing the active compounds with extenders, namelyliquid diluents; liquefied gas diluents; solid diluents or carriers, andoptionally by using surface-active agents, namely emulsifiers and/ordispersants and/or foam-forming agents.

In case that water is used as extender, for example, organic solventscan be used also as auxiliary solvents.

As liquid diluents or carriers there can be mentioned, for example,aromatic hydrocarbons (for example, xylene, toluene, alkylnaphthaleneetc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (forexample, chlorobenzenes, ethylene chlorides, methylene chloride, etc.),aliphatic hydrocarbons [for example, cyclohexane etc. or paraffins (forexample, mineral oil fractions etc.)], alcohols (for example, butanol,glycols and their ethers, esters, etc.), ketones (for example, acetone,methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.),strongly polar solvents (for example, dimethylformamide, dimethylsulfoxide, etc.), and water.

Liquefied gas diluents or carriers are substances that are gases atnormal temperature and pressure and there can be mentioned, for example,aerosol propellants such as butane, propane, nitrogen gas, carbondioxide, halogenated hydrocarbons.

As solid diluents there can be mentioned, for example, ground naturalminerals (for example, kaolin, clay, talc, chalk, quartz, attapulgite,montmorillonite, diatomaceous earth, etc.), ground synthetic minerals(for example, highly dispersed silicic acid, alumina, silicates, etc.).

As solid carriers for granules there can be mentioned, for example,crushed and fractionated rocks (for example, calcite, marble, pumice,sepiolite, dolomite, etc.) synthetic granules of inorganic and organicmeals, particles of organic materials (for example, saw dust, coconutshells, maize cobs, tobacco stalks, etc.) etc.

As emulsifiers and/or foam-forming agents there can be mentioned, forexample, nonionic and anionic emulsifiers [for example, polyoxyethylenefatty acid esters, polyoxyethylene fatty acid alcohol ethers (forexample, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates,arylsulfonates, etc.)], albumin hydrolysis products, etc.

Dispersants include, for example, lignin sulfite waste liquor and methylcellulose.

Tackifiers can also be used in formulations (powders, granules,emulsifiable concentrates). As said tackifiers there can be mentioned,for example, carboxymethyl cellulose, natural and synthetic polymers(for example, gum Arabic, polyvinyl alcohol, polyvinyl acetate, etc.).

Colorants can also be used. As said colorants there can be mentioned,for example, inorganic pigments (for example, iron oxide, titaniumoxide, Prussian Blue, etc,), organic dyestuffs such as alizarindyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, and furthertraces nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

Said formulations can contain the aforementioned active components ofthe amount in the range of generally 0.1-95% by weight, preferably0.5-90% by weight

The active compounds of the formula (I) of the present invention canexist also as a mixed agent with other active compounds, for example,insecticides, poisonous baits, bactericides, miticides, nematicides,fungicides, growth regulators or herbicides in the form of theircommercially useful formulations or in the application forms preparedfrom such formulations. Here, as the above-mentioned insecticides, therecan be mentioned, for example, organophosphorous agents, carbamateagents, carboxylate type chemicals, chlorinated hydrocarbon typechemicals, insecticidal substances produced by microbes, etc.

Further, the active compounds of the formula (I) of the presentinvention can exist also as a mixed agent with a synergist and suchformulations and application forms can be mentioned as commerciallyuseful. Said synergist itself must not be active, but is a compound thatenhances the action of the active compound.

The content of the active compounds of the formula (I) of the presentinvention in a commercially useful application form can be varied in awide range.

The concentration of the active compounds of the formula (I) of thepresent invention at the time of application can be, for example, in therange of 0.0000001-100% by weight, preferably in the range of 0.00001-1%by weight

The compounds of the formula (I) of the present invention can be used byusual methods suitable to the application forms.

In case of application against hygienic pests and stored grain pests theactive compounds of the present invention have a good stability againstalkali on a calcific substance and further show an excellent residualeffectiveness in wood and soil.

Then the present invention will be described more specifically byexamples. The present invention, however, should not be restricted onlyto them in any way.

EXAMPLES Synthesis Example 1

3-(1,1-Dimethyl-2-methylthioethylimino)-4-iodo-3H-isobenzofuran-1-one(0.94 g) and1-(4-amino-3-methylbenzyl)-4-(4-trifluoromethylphenyl)-1,4-dihydrotetrazol-5-one(0.87 g) were dissolved in dichloromethane (10 ml), to whichp-toluenesulfonic acid monohydrate (0.01 g) was added, and the mixturewas stirred at room temperature for 3 hours. After finishing thereaction, water was added to the mixture and the organic layer wasseparated and dried with anhydrous magnesium sulfate. The solvent wasdistilled off under reduced pressure and the residue was purified bysilica gel column chromatography to obtainN²-(1,1-dimethyl-2-methylthioethyl)-3-iodo-N′-[2-methyl-4-(5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-1-ylmethyl)phenyl]phthalamide(0.6 g, mp. 83-87° C.).

Synthesis Example 2

N′-{4-[4-3,5-bis-trifluoromethylphenyl)-5-oxo-4,5-dihydrotetrazol-1-ylmethyl]-2-methyl-phenyl}-N²-(1,1-dimethyl-2-methylthioethyl)-3-iodo-phthalamide(0.5 g) was dissolved in dichloromethane, to which m-chloroperbenzoicacid (0.18 g) was added, and the mixture was stirred at room temperaturefor 5 hours. After finishing the reaction the mixture was washedsuccessively with aqueous solution of sodium thiosulfate, saturatedaqueous solution of sodium hydrogen carbonate and saturated aqueoussolution of sodium chloride and dried with anhydrous magnesium sulfate.After the solvent was distilled off, the obtained residue was purifiedby silica gel column chromatography to obtainN′-{4-[4-(3,5-bis-trifluoromethylphenyl)-5-oxo-4,5-dihydrotetrazol-1-ylmethyl]-2-methyl-phenyl}-3-iodo-N²-(2-methanesulfinyl-1,1-dimethylethyl)phthalamide(0.1 g, mp. 165-171° C.).

Synthesis Example 3

N²-(1,1-Dimethyl-2-methylthioethyl)-3-iodo-N-1-[2-methyl(5-oxo-4-(fluoromethylphenyl)-4,5-dihydrotetrazol-1-ylmethyl)phenyl]phthalamide(0.4 g) was dissolved in dichloromethane, to which m-chloroperbenzoicacid (0.24 g) was added, and the mixture was stirred at room temperaturefor 5 hours. After finishing the reaction the mixture was washedsuccessively with aqueous solution of sodium thiosulfate, saturatedaqueous solution of sodium hydrogen carbonate and saturated aqueoussolution of sodium chloride and dried with anhydrous magnesium sulfate.After the solvent was distilled off, the obtained residue was purifiedby silica gel column chromatography to obtain3-iodo-N²-(2-methanesulfonyl-1,1-dimethylethyl)-N¹-{2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-1-ylmethyl]phenyl}phthalamide(0.16 g, mp. 108-112° C.).

Synthesis Example 4

2-{2-Methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-1-ylmethyl]phenyl}isoindol-1,3-dione(0.25 g) was dissolved in sec-butylamine (5 ml) and the mixture wasstirred at room temperature for 5 hours. After finishing the reaction,the solvent was distilled off under reduced pressure and the obtainedresidue was purified by silica gel column chromatography to obtain theobjectedN-sec-butyl-N-{2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-1-ylmethyl]phenyl}phthalamide(0.2 g, mp. 217-218° C.).

Examples of the compounds of the formula (I) of the present inventionobtained in the similar manner to the Synthesis Examples 1 to 4 and thecompounds of the formula (I) obtained easily by the preparationprocesses (a) to (f) are shown in the Table 1 to Table 4, together withthe compounds obtained in the above-mentioned Synthesis Examples 1 to 4.

In all tables the abbreviations mean

Ph=phenyl, Me=methyl, Et=ethyl, n-Pr=n-propyl, i-Pr=iso-propyl. TABLE 1

Q represents the following structures:

(wherein the bond marked with * connects with A¹ and the bond markedwith # connects with A²) Comp. m.p. No. R¹ R² R³ X_(n) Y_(m) A¹ Q A² E(° C.) 1-1 i-Pr H H 3-I 2-Me — Q17-1 — Ph-4-Cl 1-2 C(Me)₂CH₂SMe H H 3-I2-Me — Q17-1 — Ph-4-CF₃ 1-3 i-Pr H H 3-I 2-Me — Q34-1 — Ph-4-CF₃ 1-4i-Pr H H 3-I 2-Me — Q35-1 — Ph-4-Cl 1-5 i-Pr H H 3-I 2-Me — Q35-1 —Ph-4-CF₃ 1-6 C(Me)₂CH₂SMe H H 3-I 2-Me — Q48-1 — Ph-4-CF₃ 1-7C(Me)₂CH₂SMe H H 3-I 2-Me — Q48-2 — Ph-4-CF₃ 1-8 C(Me)₂CH₂SMe H H 3-I2-Me — Q50 — Ph-4-CF₃ 1-9 C(Me)₂CH₂SMe H H 3-I 2-Me — Q59-1 — Ph-4-CF₃1-10 C(Me)₂CH₂SMe H H 3-I 2-Me — Q60-1 — Ph-4-CF₃ 1-11 CH(Me)CH₂SMe H H3-I 2-Me — Q50 — Ph-3,5-(CF₃)₂ 228-231

TABLE 2

Q represents the following structures:

(wherein the bond marked with * connects with A¹ and the bond markedwith # connects with A²) Comp. m.p. No. R¹ R² R³ X_(n) Y_(m) A¹ Q A² E(° C.) 2-1 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q15-1 — Ph-4-CF₃ 83-89 2-2C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q15-2 — Ph-4-CF₃ 2-3 C(Me)₂CH₂SMe H H 3-I2-Me CH₂ Q22-1 — Ph-4-Cl 2-4 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q23-1 — Ph2-5 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q29-1 — Ph-4-Cl 2-6 C(Me)₂CH₂SMe H H3-I 2-Me CH₂S Q45-1 — Ph-2,4-Cl₂ 2-7 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q55-1— Ph-4-CF₃ 88-89 2-8 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q55-1 — Ph-3,5-(CF₃)₂114-117 2-9 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q56-1 — Ph-2-Cl  1) 2-10C(Me)₂CH₂SMe H H 3-I 2-Me CH₂S Q56-2 — Ph 105-107 2-11 C(Me)₂CH₂SMe H H3-I 2-Me CH₂ Q58-1 — Ph-4-Cl 2-12 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q59-1 —Ph-4-CF₃ 118-120 2-13 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q60-1 — Ph-4-CF₃  2)2-14 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q61-1 — Ph-3,5-(CF₃)₂ 2-15C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q62-1 — Ph-4-CF₃  3) 2-16 C(Me)₂CH₂SMe H H3-I 2-Me CH₂ Q63 — Ph-4-CF₃ 131-134 2-17 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂Q64-1 — Ph-2-F 92-95 2-18 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-1 — Ph-2-Cl 4) 2-19 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q64-1 — Ph-2-Cl  5) 2-20C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-1 — Ph-2-CF₃ 126-129 2-21 C(Me)₂CH₂SMeH H 3-I 2-Me CH₂ Q64-1 — Ph-3-Cl 88-93 2-22 C(Me)₂CH₂SMe H H 3-I 2-MeCH₂ Q64-1 — Ph-3-F 87-93 2-23 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q64-1 —Ph-3-Cl  98-101 2-24 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q64-1 — Ph-3-F116-120 2-25 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-1 — Ph-4-Cl 102-104 2-26C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q64-1 — Ph-4-Cl 131-134 2-27CH(Me)CH₂OMe H H 3-I 2-Me CH₂ Q64-1 — Ph-4-CF₃ 2-28 CH(Me)CH₂SMe H H 3-I2-Me CH₂ Q64-1 — Ph-4-CF₃ 2-29 CH(Me)CH₂SOMe H H 3-I 2-Me CH₂ Q64-1 —Ph-4-CF₃ 2-30 CH(Me)CH₂SO₂Me H H 3-I 2-Me CH₂ Q64-1 — Ph-4-CF₃ 2-31C(Me)₂CH₂NHCOMe H H 3-I 2-Me CH₂ Q64-1 — Ph-4-CF₃ 2-32 C(Me)₂CH₂NHCO₂MeH H 3-I 2-Me CH₂ Q64-1 — Ph-4-CF₃ 2-33 C(Me)₂CH═NOMe H H 3-I 2-Me CH₂Q64-1 — Ph-4-CF₃ 2-34 C(Me)₂CH₂CH═NOMe H H 3-I 2-Me CH₂ Q64-1 — Ph-4-CF₃2-35 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-1 — Ph-4-CF₃ 102-104 2-36CH(Me)CH₂OMe H H 3-I 2-Me CH₂ Q64-1 — Ph-3,5-(CF₃)₂ 2-37 CH(Me)CH₂NHOOMeH H 3-I 2-Me CH₂ Q64-1 — Ph-3,5-(CF₃)₂ 2-38 CH(Me)CH₂SMe H H 3-I 2-MeCH₂ Q64-1 — Ph-3,5-(CF₃)₂ 2-39 CH(Me)CH₂SO₂Me H H 3-I 2-Me CH₂ Q64-1 —Ph-3,5-(CF₃)₂ 2-40 C(Me)₂CH₂NHCOMe H H 3-I 2-Me CH₂ Q64-1 —Ph-3,5-(CF₃)₂ 2-41 C(Me)₂CH₂NHCO₂Me H H 3-I 2-Me CH₂ Q64-1 —Ph-3,5-(CF₃)₂ 2-42 C(Me)₂CH═NOMe H H 3-I 2-Me CH₂ Q64-1 — Ph-3,5-(CF₃)₂2-43 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-1 — Ph-3,5-(CF₃)₂ 2-44C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-2 — Ph-4-CF₃ 89-92 2-45 C(Me)₂CH₂SO₂MeH H 3-OSO₂Me 2-Me CH₂ Q64-1 — Ph-2-Cl  6) 2-46 C(Me)₂CH₂SMe H H 3-I 2-MeCH₂ Q64-3 — Ph-2-Cl  97-102 2-47 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-5 —Ph-2-Cl 123-127 2-48 C(Me)₂CH₂SC₂Me H H 3-I 2-Me CH₂ Q64-3 — Ph-2-Cl135-139 2-49 CH(Me)CH₂SMe H H 3-I 2-Me CH₂ Q64-3 — Ph-4-CF₃ 2-50C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-3 — Ph-4-CF₃ 98-99 2-51 CH(Me)CH₂SMe HH 3-I 2-Me CH₂ Q64-3 — Ph-3,5-(CF₃)₂ 2-52 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂Q64-3 — Ph-3,5-(CF₃)₂ 2-53 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-5 —Ph-4-CF₃ 121-126 2-54 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-4 — Ph-4-CF₃95-98 2-55 C(Me)₂CH₂SC₂Me H H 3-I 2-Me CH₂ Q64-3 — Ph-4-CF₃ 144-149 2-56Et H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 2-57 Et Et H H 2-Me CH₂ Q66 — Ph-4-CF₃2-58 n-Pr H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 179-180 2-59 i-Pr H H H 2-Me CH₂Q66 — Ph-4-CF₃  7) 2-60 CH₂CH₂CH₂CH₃ H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 2-61CH(Me)Et H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 217-218 2-62 CH₂CH₂CH₂CH₂CH₃ H HH 2-Me CH₂ Q66 — Ph-4-CF₃ 2-63 CH(Et)₂ H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 2102-64 CH(Me)n-Pr H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 193-194 2-65CH(Me)CH₂CH(Me)₂ H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 136-138 2-66CH₂-cyclohexyl H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 167-168 2-67 CH(Me)CH₂SMe HH H 2-Me CH₂ Q66 — Ph-4-CF₃ 166-169 2-68 CH(Me)CH₂SOMe H H H 2-Me CH₂Q66 — Ph-4-CF₃ 2-69 CH(Me)CH₂SO₂Me H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 197-1982-70 C(Me)₂CH₂SMe H H H 2-Me CH₂ Q66 — Ph-4-CF₃  8) 2-71 C(Me)₂CH₂SOMe HH H 2-Me CH₂ Q66 — Ph-4-CF₃ 89-92 2-72 C(Me)₂CH₂SO₂Me H H H 2-Me CH₂ Q66— Ph-4-CF₃ 156-162 2-73 cyclopropyl H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 2042-74 cyciopentyl H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 173-177 2-75 cyclohexyl HH H 2-Me CH₂ Q66 — Ph-4-CF₃ 111-112 2-76 cyclohexyl-3-Me H H H 2-Me CH₂Q66 — Ph-4-CF₃ 191-193 2-77 n-Pr H H H 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-78I-Pr H H H 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 193-195 2-79 CH₂CH₂CH₂CH₃ H H H2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-80 CH(CH₃)Et H H H 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ 2-81 C(Me)₃ H H H 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 190-1942-82 CH₂CH₂CH₂CH₂CH₃ H H H 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-83CH(Me)CH₂CH(Me)₂ H H H 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-84 CH(Me)CH₂SMe HH H 2-Me CH₂ Q66 — Ph-3.5-(CF₃)₂ 130-133 2-85 CH(Me)CH₂SCMe H H H 2-MeCH₂ Q66 — Ph-3,5-(CF₃)₂ 2-86 CH(Me)CH₂SC₂Me H H H 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ 159-163 2-87 C(Me)₂CH₂SMe H H H 2-Me CH₂ Q66 —Ph-3,5-(CF₃₎ ₂ 105-107 2-86 C(Me)₂CH₂SC₂Me H H H 2-Me CH₂ Q66 —Ph-3,5-(CF₃₎ ₂ 169-170 2-89 i-Pr H H 3-F 2-Me CH₂ Q66 — Ph-3-CF₃ 2-90C(Me)₂CH₂SMe H H 3-F 2-Me CH₂ Q66 — Ph-3-CF₃ 2-91 C(Me)₂CH₂SOMe H H 3-F2-Me CH₂ Q66 — Ph-3-CF₃ 2-92 C(Me)₂CH₂SO₂Me H H 3-F 2-Me CH₂ Q66 —Ph-3-CF₃ 2-93 i-Pr H H 3-F 2-Me CH₂ Q66 — Ph-4-CF₃ 2-94 C(Me)₂CH₂SMe H H3-F 2-Me CH₂ Q66 — Ph-4-CF₃ 57-69 2-95 C(Me)₂CH₂SOMe H H 3-F 2-Me CH₂Q66 — Ph-4-CF₃ 2-96 C(Me)₂CH₂SO₂Me H H 3-F 2-Me CH₂ Q66 — Ph-4-CF₃212-217 2-97 i-Pr H H 3-F 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-98 C(Me)₂CH₂SMeH H 3-F 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 165-167 2-99 C(Me)₂CH₂SOMe H H 3-F2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-100 C(Me)₂CH_(2SO) ₂Me H H 3-F 2-Me CH₂Q66 — Ph-3,5-(CF₃)₂ 2-101 i-Pr H H 3-Cl 2-Me CH₂ Q66 — Ph-2-Cl 2-102i-Pr H H 3-Cl 2-Me CH₂ Q66 — Ph-3-CF₃ 2-103 CH(Me)CH₂SMe H H 3-Cl 2-MeCH₂ Q66 — Ph-3-CF₃ 2-104 CH(Me)CH₂SOMe H H 3-Cl 2-Me CH₂ Q66 — Ph-3-CF₃2-105 CH(Me)CH₂SO₂Me H H 3-Cl 2-Me CH₂ Q66 — Ph-3-CF₃ 2-1Q6 C(Me)₂CH₂SMeH H 3-Cl 2-Me CH₂ Q66 — Ph-3-CF₃ 2-107 C(Me)₂CH₂SOMe H H 3-Cl 2-Me CH₂Q66 — Ph-3-CF₃ 2-108 C(Me)₂CH₂SO₂Me H H 3-Cl 2-Me CH₂ Q66 — Ph-3-CF₃2-109 i-Pr H H 3-Cl 2-Me CH₂ Q66 — Ph-4-CF₃ 2-110 CH(Me)CH₂SMe H H 3-Cl2-Me CH₂ Q66 — Ph-4-CF₃ 2-111 CH(Me)CH₂SOMe H H 3-Cl 2-Me CH₂ Q66 —Ph-4-CF₃ 2-112 CH(Me)CH₂SO₂Me H H 3-Cl 2-Me CH₂ Q66 — Ph-4-CF₃ 2-113C(Me)₂CH₂SMe H H 3-Cl 2-Me CH₂ Q66 — Ph-4-CF₃ 2-114 C(Me)₂CH₂SOMe H H3-Cl 2-Me CH₂ Q66 — Ph-4-CF₃ 2-115 C(Me)₂CH₂SO₂Me H H 3-Cl 2-Me CH₂ Q66— Ph-4-CF₃ 2-116 i-Pr H H 3-Cl 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-117CH(Me)CH₂SMe H H 3-Cl 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 93-96 2-118CH(Me)CH₂SOMe H H 3-Cl 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-119 CH(Me)CH₂SO₂MeH H 3-Cl 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 108-111 2-120 C(Me)₂CH₂SMe H H3-Cl 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 100-103 2-121 C(Me)₂CH₂SOMe H H 3-Cl2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-122 C(Me)₂CH₂SO₂Me H H 3-Cl 2-Me CH₂ Q66— Ph-3,5-(CF₃)₂ 100-105 2-123 i-Pr H H 3-Cl 2-Me CH₂ Q66 —Ph-3-OCF₂CF₂O-4 2-124 i-Pr H H 3-Br 2-Me CH₂ Q66 — Ph-4-CF₃ 2-125CH(Me)CH₂SMe H H 3-Br 2-Me CH₂ Q66 — Ph-4-CF₃ 2-126 CH(Me)CH₂SOMe H H3-Br 2-Me CH₂ Q66 — Ph-4-CF₃ 2-127 CH(Me)CH₂SC₂Me H H 3-Br 2-Me CH₂ Q66— Ph-4-CF₃ 2-128 C(Me)₂CH₂SMe H H 3-Br 2-Me CH₂ Q66 — Ph-4-CF₃ 2-129C(Me)₂CH₂SOMe H H 3-Br 2-Me CH₂ Q66 — Ph-4-CF₃ 2-130 C(Me)₂CH₂SO₂Me H H3-Br 2-Me CH₂ Q66 — Ph-4-CF₃ 2-131 i-Pr H H 3-Br 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ 2-132 CH(Me)CH₂SMe H H 3-Br 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 97-102 2-133 CH(Me)CH₂SCMe H H 3-Br 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-134CH(Me)CH₂SC₂Me H H 3-Br 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 145-148 2-135C(Me)₂CH₂SMe H H 3-Br 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 90-94 2-136C(Me)₂CH₂SCMe H H 3-Br 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-137 C(Me)₂CH₂SC₂MeH H 3-Br 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ * 2-138 C(Me)₂CH₂SMe H H 3-I 2-MeCH₂ Q66 — Ph  9) 2-139 C(Me)₂CH₂SC₂Me H H 3-I 2-Me CH₂ Q66 — Ph 10)2-140 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-2-F 82-86 2-141C(Me)₂CH,SC₂Me H H 3-I 2-Me CH₂ Q66 — Ph-2-F 128-130 2-142 i-Pr H H 3-I2-Me CH₂ Q66 — Ph-2-Cl 11) 2-143 i-Pr H H 3-I H CH₂ Q66 — Ph-2-Cl 12)2-144 CH(Me)CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-2-Cl 2-145 CH(Me)CH₂SMe HEt 3-I 2-Me CH₂ Q66 — Ph-2-Cl 2-146 CH(Me)CH₂SMe H i-Pr 3-I 2-Me CH₂ Q66— Ph-2-Cl 2-147 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-2-Cl 100-1032-148 C(Me)₂CH₂NHCO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-2-Cl 2-149C(Me)₂CH═NOMe H H 3-I 2-Me CH₂ Q66 — Ph-2-Cl 2-150 C(Me)₂CH₂SMe H H 3-I2-Me CH(Me) Q66 — Ph-2-Cl 101-104 2-151 C(Me)₂CH₂SMe H H 3-I H CH₂ Q66 —Ph-2-Cl 13) 2-152 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-2-Cl  98-1032-153 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-2-Me 14) 2-154C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-2-Me 180-182 2-155 C(Me)₂CH₂SMeH H 3-I 2-Me CH₂ Q66 — Ph-2-CF₃  96-100 2-156 C(Me)₂CH₂SO₂Me H H 3-I2-Me CH₂ Q66 — Ph-2-CF₃ 139-146 2-157 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66— Ph-2-OMe 93-94 2-158 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-2-OCF₃ 15)2-159 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-2-OCF₃ 237-239 2-160C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3-Cl 79-83 2-161 C(Me)₂CH₂SMe H H3-I 2-Me CH₂ Q66 — Ph-3-F 79-82 2-162 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂Q66 — Ph-3-Cl 114-115 2-163 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-3-F95-98 2-164 Et Et H 3-I 2-Me CH₂ Q66 — Ph-3-CF₃ 2-165 i-Pr H H 3-I 2-MeCH₂ Q66 — Ph-3-CF₃ 2-166 CH(Me)CH₂CN H H 3-I 2-Me CH₂ Q66 — Ph-3-CF₃2-167 CH(Me)CH₂CONHMe H H 3-I 2-Me CH₂ Q66 — Ph-3-CF₃ 2-168 CH(Me)CH₂OMeH H 3-I 2-Me CH₂ Q66 — Ph-3-CF₃ 2-169 CH(Me)CH₂SMe H H 3-I 2-Me CH₂ Q66— Ph-3-CF₃  98-101 2-170 CH(Me)CH₂SOMe H H 3-I 2-Me CH₂ Q66 — Ph-3-CF₃2-171 CH(Me)CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-3-CF₃ 101-105 2-172C(Me)₂CH₂SMe H H 3-I H CH₂ Q66 — Ph-3-CF₃ 156-159 2-173 C(Me)₂CH₂SMe H H3-I 2-Me CH₂ Q66 — Ph-3-CF₃ 92-93 2-174 C(Me)₂CH₂SMe H H 3-I 2-MeO(CH₂)₂ Q66 — Ph-3-CF₃ 2-175 C(Me)₂CH₂SOMe H H 3-I 2-Me CH₂ Q66 —Ph-3-CF₃ 2-176 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-3-CF₃  99-1102-177 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3-OCHF₂ 87-96 2-178C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-3-OCHF₂ 165-168 2-179C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3-OCF₃ 86-89 2-180 C(Me)₂CH₂SO₂MeH H 3-I 2-Me CH₂ Q66 — Ph-3-OCF₃ 170-172 2-181 C(Me)₂CH₂SMe H H 3-I 2-MeCH₂ Q66 — Ph-4-F 77-80 2-182 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 —Ph-4-F 148-158 2-183 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-4-Cl 78-832-184 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-4-Cl 141-143 2-185C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-4-Br 185-186 2-186 C(Me)₂CH₂SMe HH 3-I 2-Me CH₂ Q66 — Ph-4-Me 152-159 2-187 C(Me)₂CH₂SO₂Me H H 3-I 2-MeCH₂ Q66 — Ph-4-Me 192-193 2-188 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-4-i-Pr 89-95 2-189 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-4-i-Pr194-196 2-190 Et Et H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-191 i-Pr H H 3-I2-Me CH₂ Q66 — Ph-4-CF₃ 16) 2-192 i-Pr H H 3-I 2-CF₃ CH₂ Q66 — Ph-4-CF₃2-193 i-Pr H H 3-I 2-Cl CH₂ Q66 — Ph-4-CF₃ 2-194 i-Pr H H 3-I 2,3-Cl₂CH₂ Q66 — Ph-4-CF₃ 2-195 i-Pr H Me 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-196i-Pr H Et 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-197 CH(Me)CH₂CN H H 3-I 2-Me CH₂Q66 — Ph-4-CF₃ 2-198 CH(Me)CH₂CONHMe H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃2-199 CH(Me)CH₂CON(Et)₂ H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-200CH(Me)CH₂CSNHEt H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-201 CH(Me)CH₂NHCOMe HH 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-202 CH(Me)CH₂N(Me)SC₂Me H H 3-I 2-Me CH₂Q66 — Ph-4-CF₃ 2-203 CH(Me)CH₂OMe H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-204CH(Me)CH₂OEt H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-205 CH(Me)CH₂CH₂OMe H H3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-206 CH(Me)CH₂CH₂OEt H H 3-I 2-Me CH₂ Q66 —Ph-4-CF₃ 2-207 CH(Me)CH₂OCONHEt H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-208CH(Me)CH₂OCONEt₂ H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-209 CH(Me)CH₂SMe H H3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 17) 2-210 CH(Me)CH₂SMe H H 3-I 2-Cl CH₂ Q66— Ph-4-CF₃ 2-211 CH(Me)CH₂SMe H Et 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-212CH(Me)CH₂SMe H i-Pr 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-213 CH(Me)CH₂SCMe H H3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-214 CH(Me)CH₂SC₂Me H H 3-I 2-Me CH₂ Q66 —Ph-4-CF₃ 213-214 2-215 CH(Me)CH₂SCONHEt H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃2-216 CH(Me)CH₂SCSNHEt H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-217CH(Me)CH₂SO₂NHEt H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-218 CH(Me)CH₂SO₂NEt₂H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-219 C(Me)₂CH₂SMe H H 3-I H CH₂ Q66 —Ph-4-CF₃ 158-160 2-220 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃83-87 2-221 C(Me)₂CH₂SMe H H 3-I 2-Me O(CH₂)₂ Q66 — Ph-4-CF₃ 2-222C(Me)₂CH₂SMe H Et 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 180-184 2-223 C(Me)₂CH₂SMeH H 3-I 2-Cl CH₂ Q66 — Ph-4-CF₃ 125-130 2-224 C(Me)₂CH₂SMe H H 3-I 3-ClCH₂ Q66 — Ph-4-CF₃ 121-125 2-225 C(MehCH₂SOMe H H 3-I 2-Me CH₂ Q66 —Ph-4-CF₃ 2-226 C(Me)₂CH₂SOMe H H 3-I 2-Cl CH₂ Q66 — Ph-4-CF₃ 2-227C(Me)₂CH₂SC₂Me H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 108-112 2-228C(Me)₂CH₂NHCOMe H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-229 C(Me)₂CH₂NHCO₂Me HH 3-I 2-Me CH₂ Q66 — Ph-A-CF₃ 2-230 C(Me)₂CH═NOMe H H 3-I 2-Me CH₂ Q66 —Ph-4-CF₃ 2-231 C(Me)₂CH₂CH═NOMe H H 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 2-232C(Me)₂CH₂SC₂Me H H 3-I 2-Cl CH₂ Q66 — Ph-4-CF₂ 159-165 2-233C(Me)₂CH₂SC₂Me H H 3-I H CH₂ Q66 — Ph-4-CF₃ 161-163 2-234 C(Me)₂CH₂SMe HH 3-I 2-Me CH₂ Q66 — Ph-4-OCF₃ 117-119 2-235 C(Me)₂CH₂SMe H H 3-I 2-MeCH₂ Q66 — Ph-4-SCF₃ 2-236 C(Me)₂CH₂SC₂Me H H 3-I 2-Me CH₂ Q66 —Ph-4-SCF₃ 2-237 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-4-(Ph-4-CF₃)2-238 C(Me)₂CH₂SC₂Me H H 3-I 2-Me CH₂ Q66 — Ph-4-(Ph-4-CF₃) 2-239C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-4-[Ph-3,5-(CF₃)₂] 110-117 2-240C(Me)₂CH₂SC₂Me H H 3-I 2-Me CH₂ Q66 — Ph-4-[Ph-3,5-(CF₃)₂] 127-131 2-241C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-2-F-3-CF₃ 107 2-242 C(Me)₂CH₂SMeH H 3-I 2-Me CH₂ Q66 — Ph-2-F-4-Br 80-82 2-243 C(Me)₂CH₂SMe H H 3-I 2-MeCH₂ Q66 — Ph-3-F-5-CF₃ 79-84 2-244 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-2-F-5-CF₃ 190-194 2-245 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-3-Br-4-OCF₃ 143-146 2-246 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-2-Cl-5-CF₃ 97-99 2-247 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-3-CF₃-4-Cl 95-99 2-248 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-3-Cl-4-OCF₃ 147-149 2-249 C(Me)₂CH₂SC₂Me H H 3-I 2-Me CH₂ Q66 —Ph-3-Cl-4-OCF₃ 18) 2-250 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-3-CF₃-4-F 86-90 2-251 C(Me)₂CH₂SC₂Me H H 3-I 2-Me CH₂ Q66 —Ph-3-CF₃-4-F 179-189 2-252 i-Pr H H 3-I 2-Me CH₂ Q66 — Ph-3,4-(CF₃)₂2-253 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3,4-(CF₃)₂ 112-118 2-254C(Me)₂CH₂SOMe H H 3-I 2-Me CH₂ Q66 — Ph-3,4-(CF₃)₂ 2-255 C(Me)₂CH₂SC₂MeH H 3-I 2-Me CH₂ Q66 — Ph-3,4-(CF₃)₂ 2-256 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂Q66 — Ph-3,5-Cl₂ 145-147 2-257 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-3,5-(CMe)₂ 2-258 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3-CF₃-5-F107-112 2-259 Et H Et 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-260 i-Pr H H3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 195-196 2-261 CH(Me)CH₂CN H H 3-I 2-MeCH₂ Q66 — Ph-3,5-(CF₃)₂ 2-262 CH(Me)CH₂CONHMe H H 3-I 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ 2-263 CH(Me)CH₂CONEt₂ H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂2-264 CH(Me)CH₂NHCOMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-265CH(Me)CH₂OMe H H 3-I 2-Me CH₂ Q66 — Ph-3~5-(CF₃)₂ 86-89 2-266CH(Me)CH₂OEt H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-267 CH(Me)CH₂CH₂CMeH H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-268 CH(Me)CH₂CH₂CEt H H 3-I 2-MeCH₂ Q66 — Ph-3,5-(CF₃)₂ 2-269 CH(Me)CH₂OCONHEt H H 3-I 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ 2-270 CH(Me)CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂101-103 2-271 CH(Me)CH₂SMe H Et 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-272CH(Me)CH₂SMe H H 3-I 2-Cl CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-273 CH(Me)CH₂SCMe HH 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ * 2-274 CH(Me)CH₂SC₂Me H H 3-I 2-MeCH₂ Q66 — Ph-3,5-(CF₃)₂ 187-190 2-275 C(Me)₂CH₂NHCOMe H H 3-I 2-Me CH₂Q65 — Ph-3,5-(CF₃)₂ 2-276 C(Me)₂CH₂NHCO₂Me H H 3-I 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ 2-277 C(Me)₂OH═NOMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂2-278 C(Me)₂OH₂OH═NOMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-279C(Me)₂CH₂OCSNHMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-280C(Me)₂CH₂OCSNMe₂ H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-281 C(Me)₂CH₂SMeH H 3-I 2-Me CH(Me) Q66 — Ph-3,5-(CF₃)₂ 118-122 2-282 C(Me)₂CH₂SMe H H3-I 2-OMe CH₂ Q66 — Ph-3,5-(CF₃)₂ 133-137 2-283 C(Me)₂CH₂SMe H H 3-I3-Cl CH₂ Q66 — Ph-3,5-(CF₃)₂ 76-80 2-284 C(Me)₂CH₂SMe H H 3-I 3-OMe CH₂Q66 — Ph-3,5-(CF₃)₂ 104-108 2-285 C(Me)₂CH₂SMe H H 3-I 2,6-Me₂ CH₂ Q66 —Ph-3,5-(CF₃)₂ 102-104 2-286 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ 115-117 2-287 C(Me)₂CH₂SMe H H 3-I 2-Cl CH₂ Q66 —Ph-3,5-(CF₃)₂ 2-288 C(Me)₂CH₂SMe H Et 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂84-87 2-289 C(Me)₂CH₂SOMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 165-1712-290 C(Me)₂CH₂SOMe H H 3-I 2-Cl CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-291C(Me)₂CH₂SO₂Me H H 3-I 2-OMe CH₂ Q66 — Ph-3,5-(CF₃)₂ 74-78 2-292C(Me)₂CH₂SO₂Me H H 3-I 2,6-Me₂ CH₂ Q66 — Ph-3,5-(CF₃)₂ 171-173 2-293C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 116-118 2-294C(Me)₂CH₂SO₂Me H H 3-I 2-Cl CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-295 C(Me)₂CH₂SMe HH 3-I 2-Me CH₂ Q66 — Ph-2-OMe-3-Cl-5-Me 94-96 2-296 C(Me)₂CH₂SO₂Me H H3-I 2-Me CH₂ Q66 — Ph-2-OMe-3-Cl-5-Me 152-153 2-297 C(Me)₂CH₂SMe H H 3-I2-Me CH₂ Q66 — Ph-2,6-Et₂-3,4-Cl₂ 95-97 2-298 C(Me)₂CH₂SMe H H 3-I 2-MeCH₂ Q66 — Ph-3-OCF₂O-4 2-299 C(Me)₂CH₂SOMe H H 3-I 2-Me CH₂ Q66 —Ph-3-OCF₂O-4 2-300 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q68 — Ph-3-OCF₂O-42-301 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3-OCHFOF₂O-4 2-302C(Me)₂CH₂SOMe H H 3-I 2-Me CH₂ Q66 — Ph-3-OCHFOF₂O-4 2-303C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-3-OCHFOF₂O-4 2-304 C(Me)₂CH₂SMeH H 3-I 2-Me CH₂ Q66 — Ph-3-OCF₂CHFO-4 2-305 C(Me)₂CH₂SOMe H H 3-I 2-MeCH₂ Q66 — Ph-3-OCF₂CHFO-4 2-3Q6 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 —Ph-3-OCF₂CHFO-4 2-307 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —Ph-3-OCF₂CF₂O-4 86-88 2-308 C(Me)₂CH₂SOMe H H 3-I 2-Me CH₂ Q66 —Ph-3-OCF₂CF₂O-4 2-309 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 —Ph-3-OCF₂CF₂O-4 2-310 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-2-F- 19)4-OCF₂CF₂O-5 2-311 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-2-F- 117-1194-OCF₂CF₂O-5 2-312 CH(Me)CH₂SMe H H 3-I 2-Me CH₂ Q66 — 3-pyridine 2-313C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — 3-pyridine 2-314 CH(Me)CH₂SMe H H3-I 2-Me CH₂ Q66 — 2-thiaphene 2-315 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 —2-(thiophene-5-Cl) 2-316 C(Me)₂CH₂SMe H H 3-Me 2-Me CH₂ Q68 — Ph-3-CF₃2-317 C(Me)₂CH₂SMe H H 3-Me 2-Me CH₂ Q66 — Ph-4-CF₃ 2-318 C(Me)₂CH₂SMe HH 3-Me 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 166-173 2-319 i-Pr H H 3-CN 2-Me CH₂Q66 — Ph-3-CF₃ 2-320 i-Pr H H 3-CF₃ 2-Me CH₂ Q66 — Ph-3-CF₃ 2-321 i-Pr HH 3-NHSO₂Me 2-Me CH₂ Q66 — Ph-3-CF₃ 2-322 i-Pr H H 3-N(SO₂Me)₂ 2-Me CH₂Q66 — Ph-3-CF₃ 2-323 i-Pr H H 3-NO₂ 2-Me CH₂ Q66 — Ph-4-CF₃ 20) 2-324i-Pr H H 3-NO₂ 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-325 C(Me)₂CH₂SMe H H 3-NO₂2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-326 C(Me)₂CH₂SMe H H 3-OSO₂Me 2-Me CH₂Q66 — Ph 150-154 2-327 C(Me)₂CH₂SO₂Me H H 3-OSO₂Me 2-Me CH₂ Q66 — Ph 21)2-328 i-Pr H H 3-OSO₂Me H CH₂ Q66 — Ph-2-Cl 22) 2-329 C(Me)₂CH₂SMe H H3-OSO₂Me 2-Me CH₂ Q66 — Ph-2-Cl  94-104 2-330 C(Me)₂CH₂SO₂Me H H3-OSO₂Me 2-Me CH₂ Q66 — Ph-2-Cl 23) 2-331 C(Me)₂CH₂SMe H H 3-OSO₂Me 2-MeCH₂ Q66 — Ph-3-Cl 24) 2-332 C(Me)₂CH₂SMe H H 3-OSO₂CF₃ 2-Me CH₂ Q66 —Ph-3-Cl 2-333 C(Me)₂CH₂SMe H H 3-OSO₂Me 2-Me CH₂ Q66 — Ph-3-CF₃ 115-1192-334 C(Me)₂CH₂SO₂Me H H 3-OSO₂Me 2-Me CH₂ Q66 — Ph-3-CF₃ 170-179 2-335C(Me)₂CH₂SMe H H 3-OSO₂Me 2-Me CH₂ Q66 — Ph-4-Cl 25) 2-336C(Me)₂CH₂SO₂Me H H 3-OSO₂Me 2-Me CH₂ Q66 — Ph-4-Cl 26) 2-337C(Me)₂CH₂SMe H H 3-OSO₂Me 2-Me CH₂ Q66 — Ph-4-CF₃ 151-153 2-338C(Me)₂CH₂SMe H H 3-OSO₂Me 2-Me CH₂ Q66 — Ph-3,5-(CF₃₎ ₂ 86-88 2-339C(Me)₂CH₂SO₂Me H H 3-OSO₂Me 2-Me CH₂ Q66 — Ph-3,5-(CF₃₎ ₂ 184-185 2-340C(Me)₂CH₂SMe H H 3-OSO₂CF₃ 2-Me CH₂ Q66 — Ph-4-CF₃ 2-341 C(Me)₂CH₂SMe HH 4-Me 2-Me CH₂ Q66 — Ph-4-CF₃ 2-342 C(Me)₂CH₂SMe H H 4-Me 2-Me CH₂ Q66— Ph-3,5-(CF₃)₂ 154-156 2-343 i-Pr H H 4-NO₂ 2-Me CH₂ Q66 — Ph-4-CF₃143-148 2-344 C(Me)₂CH₂SMe H H 4-NO₂ 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-345C(Me)₂CH₂SMe H H 6-Me 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 160-164 2-346C(Me)₂CH₂SMe H H 6-I 2-Me CH₂ Q66 — Ph-4-CF₃ 218-220 2-347 C(Me)₂CH₂SMeH H 3,6-Cl₂ 2-Me CH₂ Q66 — Ph-a-CF₃ 2-348 C(Me)₂CH₂SMe H H 3,6-Cl₂ 2-MeCH₂ Q66 — Ph-4-CF₃ 2-349 C(Me)₂CH₂SMe H H 3,6-Cl₂ 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ 2-350 C(Me)₂CH₂SMe H H 4,5-Cl₂ 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ >250 2-351 C(Me)₂CH₂SO₂Me H H 4,5-Cl₂ 2-Me CH₂ Q66 —Ph-3,5-(CF₃)₂ 189-188 2-352 C(Me)₂CH₂SMe H H 3,4,5,6-Cl₄ 2-Me CH₂ Q66 —Ph-3-CF₃ 2-353 C(Me)₂CH₂SMe H H 3,4,5,6-Cl₄ 2-Me CH₂ Q66 — Ph-4-CF₃2-354 C(Me)₂CH₂SMe H H 3,4,5,6-Cl₄ 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2092-355 C(Me)₂CH₂SO₂Me H H 3,4,5,6-Cl₄ 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 2-356C(Me)₂CH₂SMe H H 3,4,5,6-Br₄ 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 209-210 2-357C(Me)₂CH₂SMe H H 4-C(Me)₃ 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 157-164 2-358C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q69-1 — Ph-4-CF₃ 2-359 CH(Me)CH₂SMe H H3-Cl 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂  98-102 (S)-isomer 2-360C(Me)₂CH₂SO₂Me H H 3,4,5-6,Br₄ 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 192-1952-361 CH(Me)CH₂SMe H H H 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 137-140 (S)-isomer2-362 CH(Me)CH₂SO₂Me H H H 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 186-188(S)-isomer 2-363 CH(Me)CH₂SMe H H H 2-Me CH₂ Q66 — Ph-3-CF₃ 160-1632-364 CH(Me)CH₂SO₂Me H H H 2-Me CH₂ Q66 — Ph-3-CF₃ 174-175 2-365CH(Me)CH₂SEt H H H 2-Me CH₂ Q66 — Ph-a-CF₃ 142-144 (S)-isomer 2-366CH(Me)CH₂SO₂Et H H H 2-Me CH₂ Q66 — Ph-3-CF₃ 123-129 (S)-isomer 2-367CH(Me)CH₂SEt H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 158-159 (S)-isomer 2-368CH(Me)CH₂SO₂Et H H H 2-Me CH₂ Q66 — Ph-4-CF₃ 192-195 (S)-isomer 2-369CH(Me)CH₂SEt H H H 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 144-150 (S)-isomer 2-370CH(Me)CH₂SO₂Et H H H 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 185-187 (S)-isomer2-371 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q55-1 — Ph-3,5-(CF₃)₂ 231-2322-372 CH(Me)CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 160-169(S)-isomer 2-373 CH(Me)CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂104-109 (R)-isomer 2-374 CH₂CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂196-199 2-375 CH₂CH₂SEt H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 179-1832-376 C(Me)₂CH₂SO₂Et H H 3-I 2-Me CH₂ Q66 — Ph-3-NO₂  98-100 2-377CH(Me)CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 193-195 (S)-isomer2-378 CH(Me)CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 178-187(R)-isomer 2-379 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-6 — Ph-3,5-(CF₃)₂104-111 2-380 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q55-1 — Ph-3-CF₃ 92-98 2-381C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q55-1 — Ph-3-CF₃ 183-184 2-382C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q41-1 — Ph 94-96 2-384 CH(Me)CH₂SEt H H3-I 2-Me CH₂ Q66 — Ph-3-CF₃ 77-82 (S)-isomer 2-385 CH(Me)CH₂SO₂Et H H3-I 2-Me CH₂ Q66 — Ph-3-CF₃ 118-127 (S)-isomer 2-386 CH(Me)CH₂SEt H H3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 182-185 (S)-isomer 2-387 CH(Me)CH₂SO₂Et H H3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 204-207 (S)-isomer 2-388 CH(Me)CH₂SEt H H3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 194-196 (S)-isomer 2-389 CH(Me)CH₂SO₂EtH H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 222-223 (S)-isomer 2-390CH(Me)CH₂SCH₂Et H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 91-95 (S)-isomer2-391 CH(Me)CH₂SO₂n-Pr H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 189-190(S)-isomer 2-392 CH(Et)CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂189-191 2-393 cyclhexyl-2-SMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂169-173 2-394 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q41-1 — Ph-3,5-(CF₃)₂101-106 2-395 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q15-1 — Ph-3,5-(CF₃)₂ 89-912-398 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-2 — Ph-3,5-(CF₃)₂ 116-119 2-397C(Me)₃ H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 141-144 2-398cyclopentyl-1-CH₂SMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 186-187 2-399CH₂CH(Me)SMe H H 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 103-107 2-400C(Me)₂CH₂SO₂Me H H 3-NO₂ 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 182-185 2-401CH(Me)CH₂SMe H H 3-OSO₂Me 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 88-94 2-402CH(Me)CH₂SMe H H 3-OSO₂CF₃ 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 87-94 2-403CH(Me)CH₂SMe H H 3-OSO₂Et 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 88-94 2-404CH(Me)CH₂SMe H H 3-OSO₂Ph 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 89-91 2-405CH(Me)CH₂SMe H H 3-OCO-Me 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂ 76-80 2-4Q6C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q64-6 — Ph-2-Cl 111-114 2-407C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q64-6 — Ph-2-Cl 27) 2-408 C(Me)₂CH₂SMe HH 3-I 2-Me (CH₂)₂ Q66 — Ph-3.5-(CF₃)₂ 111-120 2-409 CH(Me)CH₂SMe H H 3-I2-Me CH₂ Q66 — Ph-3,5-(CF3)₂ 105-108 2-410 CH(Me)CH₂SO₂Me H H 3-I 2-MeCH₂ Q66 — Ph-3,5-(CF3)₂ 119-121 2-411 CH(Me)CH₂SO₂Me H H 3-I 2-Me CH₂Q48-1 — Ph-3,5-(CF₃)₂ 199-202 2-412 CH(Me)CH₂SMe H H 3-I 2-Me CH₂ Q54 —Ph-3,5-(CF₃)₂ 213-214 2-413 C(Me)₂CH₂SMe H Et 3-I 2-Me CH₂ Q66 —Ph-3-CF₃ 121-123 2-414 C(Me)₂CH₂SO₂Me H Et 3-I 2-Me CH₂ Q66 — Ph-3-CF₃ 98-101 2-415 C(Me)₂CH₂SO₂Me H Et 3-I 2-Me CH₂ Q66 — Ph-4-CF₃ 112-1152-416 C(Me)₂CH₂SO₂Me H Et 3-I 2-Me CH₂ Q66 — Ph-3,5-(CF₃)₂  99-102 2-417C(Me)₂CF₃ H H 3-I 2-Me CH₂ Q55-1 — Ph-3,5-(CF₃)₂ 174-177 2-418 CH_(2CH)₂CH₂CF₃ H H 3-I 2-Me CH₂ Q55-1 — Ph-3,5-(CF₃)₂ 184-185 2-419 CH(Me)CF₃ HH 3-I 2-Me CH₂ Q55-1 — Ph-3,5-(CF₃)₂ >250 2-420 CH₂CF₂CF₃ H H 3-I 2-MeCH₂ Q55-1 — Ph-3,5-(CF₃)₂ 220-2211) ¹H-NMR (CDCl₃, ppm): 1.4 (6H, s), 1.9 (3H, s), 2.3 (3H, s), 2.8 (2H,s), 5.7 (2H, s), 6.0 (1H, s), 7.0-8.3 (11H, m)2) ¹H-NMR (CDCl₃, ppm): 1.4 (6H, s), 2.0 (3H, s), 2.2 (3H, s), 2.9 (2H,s), 4.8 (2H, s), 6.3 (1H, d), 6.4 (1H, s), 6.6 (1H, d), 7.0-8.5 (11H, m)3) ¹H-NMR (ODCl₃, ppm): 1.4 (6H, s), 2.0 (3H, s), 2.3 (3H, s), 2.8 (2H,s), 3.9 (2H, s), 4.6 (2H, s), 6.1 (1H, s), 7.0-8.4 (11H, m)4) ¹H-NMR (ODCl₃, ppm): 1.4 (6H, s), 2.0 (3H, s), 2.2 (3H, s), 2.9 (2H,s), 4.8 (2H, s), 6.1 (1H, s), 7.1-8.4 (12H, m)5) ¹H-NMR (CDCl₃, ppm): 1.6 (6H, s), 2.2 (3H, s), 2.6 (3H, s), 3.5 (2H,s), 4.9 (2H, s), 6.2 (1H, s), 7.1-8.2 (12H, m)6) ¹H-NMR (CDCl₃, ppm): 1.6 (6H, s), 2.3 (3H, s), 2.6 (3H, s), 3.3 (3H,s), 3.6 (2H, s), 4.9 (2H, s), 6.8 (1H, s), 7.1-8.1 (12H, m)7) ¹H-NMR (CDCl₃, ppm): 1.2 (6H, d), 2.3 (3H, s), 4.2 (1H, m), 5.1 (2H,s), 6.0 (1H, m), 7.2-8.6 (12H, m)8) ¹H-NMR (CDCl₃, ppm): 1.4 (6H, s), 2.1 (3H, s), 2.3 (3H, s), 3.0 (2H,s), 5.1 (2H, s), 6.1 (1H, s), 7.2-8.9 (12H, m)9) ¹H-NMR (CDCl₃, ppm): 1.4 (6H, s), 2.0 (3H, s), 2.3 (3H, s), 2.9 (2H,s), 5.1 (2H, s), 6.1 (1H, s), 7.2-8.3 (12H, m)10) ¹H-NMR (CDCl₃, ppm): 1.7 (6H, s), 2.3 (3H, s), 2.6 (3H, s), 3.5 (2H,s), 5.1 (2H, s), 6.2 (1H, s), 7.0-8.2 (12H, m)11) ¹H-NMR (DMSO-d₆, ppm): 1.0 (6H, d), 2.2 (3H, s), 4.0 (1H, m), 5.1(2H, a), 7.0-8.2 (11H, m), 9.4 (1H, s)12) ¹H-NMR (CDCl₃, ppm): 1.1 (6H, d), 4.1 (1H, m), 5.1 (2H, s), 5.9 (1H,d), 7.0-8.0 (11H, m), 8.9 (1H, s)13) ¹H-NMR (CDCl₃, ppm): 1.4 (6H, s), 2.0 (3H, s), 2.9 (2H, s), 5.1 (2H,s), 6.1 (1H, s), 7.0-8.0 (11H, m), 8.9 (1H, s)14) ¹H-NMR (CDCl₃, ppm): 1.4 (6H, s), 2.0 (3H, s), 2.2 (3H, s), 2.3 (3H,s), 2.9 (2H, s), 5.1 (2H, s), 6.0 (1H, s), 7.1-8.3 (11H, m)15) ¹H-NMR (CDCl₃, ppm): 1.4 (6H, s), 2.0 (3H, s), 2.3 (3H, s), 2.9 (2H,s), 5.1 (2H, s), 6.1 (1H, s), 7.0-8.4 (11H, m)16) ¹H-NMR (CDCl₃, ppm): 1.1 (6H, d), 2.3 (3H, s), 4.1 (1H, m), 5.1 (2H,s), 5.9 (1H, m), 7.1-8.3 (11H, m)17) ¹H-NMR (CDCl₃, ppm): 1.2 (3H, d), 2.0 (3H, s), 2.3 (3H, s), 2.7 (2H,dd), 4.1 (1H, m), 5.1 (2H, s), 6.1 (1H, d), 7.1-8.3 (11H, m)18) ¹H-NMR (CDCl₃, ppm): 1.6 (6H, s), 2.2 (3H, s), 2.6 (3H, s), 3.5 (2H,s), 5.1 (2H, s), 6.2 (1H, s), 7.1-8.1 (10H, m)19) ¹H-NMR (CDCl₃, ppm): 1.4 (6H, s), 2.0 (3H, s), 2.3 (3H, s), 2.8 (2H,s), 5.1 (2H, s), 6.1 (1H, s), 7.0-8.4 (9H, m)20) ¹H-NMR (CDCl₃, ppm): 1.1 (6H, d), 2.3 (3H, s), 4.2 (1H, m), 5.1 (2H,s), 5.9 (1H, m), 7.2-8.3 (11H,m)21) ¹H-NMR (CDCl₃, ppm): 1.6 (6H, s), 2.2 (3H, s), 2.6 (3H, s), 3.2 (3H,s), 3.5 (2H, s), 5.1 (2H, s), 6.7 (1H, s), 7.2-8.0 (12H, m)22) ¹H-NMR (CDCl₃, ppm): 1.1 (6H, d), 3.2 (3H, s), 4.1 (1H, m), 5.1 (2H,s), 6.2 (1H, d), 7.3-7.923) ¹H-NMR (CDCl₃, ppm): 1.6 (6H, s), 2.3 (3H, s), 2.6 (3H, s), 3.2 (3H,s), 3.6 (2H, s), 5.1 (2H, s), 6.7 (1H, s), 7.2-8.1 (11H, m)24) ¹H-NMR (CDCl₃, ppm): 1.3 (6H, s), 2.0 (3H, s), 2.3 (3H, s), 2.9 (2H,s), 3.3 (3H, s), 5.1 (2H, s), 6.6 (1H, s), 7.2-8.5 (11H, m)25) ¹H-NMR (CDCl₃, ppm): 1.4 (6H, s), 1.9 (3H, s), 2.3 (3H, s), 2.9 (2H,s), 3.2 (3H, s), 5.1 (2H, s), 6.3 (1H, s), 7.2-8.3 (11H, m)26) ¹H-NMR (CDCl₃, ppm): 1.6 (6H, s), 2.3 (3H, s), 2.6 (3H, s), 3.3 (3H,s), 3.7 (2H, s), 5.1 (2H, s), 6.8 (1H, s), 7.2-8.1 (11H, m)27) ¹H-NMR (CDCl₃, ppm): 1.6 (6H, s), 2.3 (3H, s), 2.6 (3H, s), 3.5 (2H,d), 5.0 (2H, s), 6.4 (1H, s), 7.1-8.2 (11H, m)

TABLE 3

Q represents the following structures:

(wherein the bond marked with * connects with A1 and the bond markedwith # connects with A²) Comp. m.p. No. R¹ R² R³ X_(n) Y_(m) A¹ Q A² E(° C.) 3-1 C(Me)₂CH₂SMe H H H 2-Me — Q15-2 CH₂ Ph-4-CF₃ 3-2 C(Me)₂CH₂SMeH H H 2-Me — Q66 CH₂ Ph 3-3 C(Me)₂CH₂SMe H H H 2-Me — Q66 CH₂CH₂ Ph-4-Cl3-4 C(Me)₂CH₂SMe H H H 2-Me — Q66 CH₂CH₂CH₂ Ph-4-Cl 3-5 C(Me)₂CH₂SMe H HH 2-Me — Q66 CH₂CH═CH Ph 3-6 C(Me)₂CH₂SMe H H 3-I 2-Me — Q66 CH₂Ph-3-CF₃ 126-131 3-7 C(Me)₂CH₂SMe H H 3-I 2-Me — Q66 CH₂ Ph-4-CF₃131-136 3-8 C(Me)₂CH₂SMe H H 3-I 2-Me — Q66 CH₂ Ph-3-OCHF₂ 117-119 3-9C(Me)₂CH₂SO₂Me H H 3-I 2-Me — Q66 CH₂ Ph-3-CF₃ 3-10 C(Me)₂CH₂SO₂Me H H3-I 2-Me — Q66 CH₂ Ph-3-OCHF₂ 3-11 C(Me)₂CH₂SO₂Me H H 3-I 2-Me — Q66 CH₂Ph-4-CF₃ 3-12 CH(Me)CH₂SMe H H 3-I 2-Me — Q50 CH₂ Ph-3,5-(CF₃)₂ 212-214

TABLE 4

Q represents the following structures:

Comp. m.p. No. R¹ R² R³ X_(n) Y_(m) A¹ Q A² E (° C.) 4-1 CH(CH₃)₂ H H3-I 2-Me CH₂ Q66 CH₂ Ph  99-103 4-2 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66CH₂ Ph 85-91 4-3 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 CH₂ Ph-4-CF₃ 90-964-4 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 CH₂ Ph-4-CF₃ 111-115 4-5C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 CH(Me) Ph-2-F 113-119 4-6 C(Me)₂CH₂SMeH H 3-I 2-Me CH₂ Q66 CH(Me) Ph-2-Cl 114-118 4-7 C(Me)₂CH₂SO₂Me H H 3-I2-Me CH₂ Q66 CH(Me) Ph-2-Cl 202-206 4-8 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂Q66 CH(Me) Ph-2-CF₃ 104-107 4-9 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 CH(Me)Ph-3-F 88-94 4-10 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 CH(Me) Ph-3-Cl 83-864-11 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 CH(Me) Ph-3-CF₃ 72-77 4-12C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 CH(Me) Ph-3-CF₃ * 4-13 C(Me)₂CH₂SMeH H 3-I 2-Me CH₂ Q66 CH(Me) Ph-4-F 92-98 4-14 C(Me)₂CH₂SMe H H 3-I 2-MeCH₂ Q66 CH(Me) Ph-4-CF₃ 85-89 4-15 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66CH(Me) Ph-4-CF₃ 111-115 4-16 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 CH(Me)Ph-2,4-F₂ 75-78 4-17 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 CH(Me) Ph-2,4-Cl₂136-139 4-18 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 CH(Me) Ph-2,4-Cl₂182-187 4-19 C(Me)₂CH₂SMe H H 3-I 2-Me CH₂ Q66 CH(Me) Ph-3,4-F₂ 87-934-20 C(Me)₂CH₂SO₂Me H H 3-I 2-Me CH₂ Q66 CH(Me) Ph-3,4-F₂ 100-108* ¹H-NMR (CDCl₃, ppm): 1.6 (6H, s), 1.9 (3H, d), 2.3 (3H, s), 2.5 (3H,s), 3.5 (2H, s), 5.0 (2H, s), 5.5 (1H, q), 6.3 (1H, s), 7.0-8.1 (11H, m)

Synthesis Example 5 Starting Material Synthesis

To an ethanol solution (100 mL) of 1-(3-methyl-4-nitrobenzyl)(4-trifluoromethylphenyl)-1,4-dihydrotetrazol-5-one (9.48 g) 10%palladium carbon (0.25 g) was added and the mixture was stirred underhydrogen atmosphere at room temperature for 6 hours. After finishing thereaction, palladium carbon was filtered off and the solvent wasdistilled off under reduced pressure to obtain1-(4-amino-3-methyl-benzyl)-4-(4-trifluoromethyl-phenyl)-1,4-dihydrotetrazol-5-one(8.11 g, mp. 210-211° C.).

Synthesis Example 6 Starting Material Synthesis

In a similar manner as Synthesis Example 5, by using1-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-1,4-dihydrotetrazol-5-one,1-(4-amino-3-methyl-benzyl)-4-(3-trifluoromethyl-phenyl)-1,4-dihydrotetrazol-5-onewas obtained (mp. 89-94° C.).

Synthesis Example 7 Starting Material Synthesis

In a similar manner as Synthesis Example 5, by using1-(3,5-bis-trifluoromethyl-phenyl)-4-(3-methyl-4-nitro-benzyl)-1,4-dihydro-tetrazol-5-one,1-(4-amino-3-methyl-benzyl)-4-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-onewas obtained (mp. 129-130° C.).

Synthesis Example 8 Starting Material Synthesis

3-Methyl-4-nitrobenzyl chloride (1.6 g),1-(4-trifluoromethylphenyl)-1,4-dihydrotetrazol-5-one (2.0 g) andpotassium carbonate (1.4 g) were stirred in DMF (50 ml) at roomtemperature for 5 hours. After finishing the reaction, water (100 ml)was added and the mixture was extracted with ethyl acetate. The organiclayer was washed with a saturated aqueous solution of sodium chloride(100 ml) and dried with magnesium sulfate. After the solvent wasdistilled off, the obtained residue was purified by silica gel columnchromatography to obtain1-(3-methyl-4-nitrobenzyl)-4-(4-trifluoromethylphenyl)-1,4-dihydrotetrazol-5-one[2.6 g, ¹H-NMR (CDCl₃, ppm); 2.6 (3H, s), 5.3 (2H, s), 7.4-8.3 (7H, m)].

Synthesis Example 9 Starting Material Synthesis

In a similar manner as Synthesis Example 8, by using1-(3-trifluoromethyl-phenyl)-4-dihydro-tetrazol-5-one,1-(3-methyl-4-nitro-benzyl)-4-(3-trifluoromethyl-phenyl)-1,4-dihydrotetrazol-5-onewas obtained [¹H-NMR (CDCl₃, ppm); 2.6 (3H, s), 5.2 (2H, s), 7.3-8.2(7H, m)].

Synthesis Example 10 Starting Material Synthesis

In a similar manner as Synthesis Example 8, by using1-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydrotetrazol-5-one in place of1-(4-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one,1-(3,5-bis-trifluoromethyl-phenyl)-4-(3-methyl-nitro-benzyl)-1,4-dihydro-tetrazol-5-onewas obtained [¹H-NMR (CDCl₃, ppm); 2.6 (3H, s), 5.2 (2H, s), 7.2-8.0(4H, m), 8.5 (2H, bs)].

Synthesis Example 11 Starting Material Synthesis

3,5-Bis(trifluoromethyl)phenyl isocyanate (10.20 g) and trimethylsilylazide (9.36 g) were stirred at 120-130° C. for 10 hours. After thereaction mixture was brought to the room temperature, excess oftrimethylsilyl azide was distilled off under reduced pressure and theobtained crude crystals were washed with petroleum ether to obtain1-(3,5-bis-trifluoromethyl-phenyl)-1,4-dihydro-tetrazol-5-one (11.05 g,mp. 145-147° C.).

Synthesis Example 12 Starting Material Synthesis

Phthalic anhydride (1.0 g) and1-(4-amino-3-methylbenzyl)-4-(4-trifluoromethylphenyl)-1,4-dihydrotetrazol-5-one(2.4 g) were refluxed in 60 ml of acetic acid for 3 hours. Afterfinishing the reaction the solvent was distilled off under reducedpressure to obtain the objected2-{2-methyl-4-[5-oxo-4-(4-trifluoromethylphenyl)-4,5-dihydrotetrazol-1-ylmethyl]phenyl}isoindol-1,3-dione[3.0 g, ¹H NMR (DMSO-d₆, ppm); 2.1 (3H, s), 5.2 (2H, s), 7.3-8.2 (1H,m)].

Synthesis Example 13 Starting Material Synthesis

1-(3-Methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)urea (1.0 g) wasdissolved in 20 ml of dichloromethane, to which 5 ml of dichloromethanesolution of oxalyl chloride (0.49 g) was added at room temperature, andthe mixture was stirred for 8 hours. After the solvent was distilled offunder reduced pressure, the obtained residue was purified by silica gelcolumn chromatography to obtain the objected1-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)imidazolidin-2,4,5-trione[1.1 g, ¹H NMR (CDCl₃, ppm); 2.6 (3H, s), 4.9 (2H, s), 7.3-8.0 (7H, m)].

Synthesis Example 14 Starting Material Synthesis

Methanol solution (5 ml) of 3-methyl-4-nitrobenzaldehyde (0.9 g) wasadded to a methanol suspension (5 ml) of glycine ethyl ester acetate(1.1 g) and sodium cyanotrihydroborate (0.53 g) at 0° C. After stirringthe mixture at room temperature for 10 hours, 2N hydrochloric acid (10ml) and ethyl acetate (10 ml) were added thereto. After removing theorganic layer, 1N aqueous solution of sodium hydroxide (30 ml) was addedto the aqueous layer and extracted with ethyl acetate. After washing theorganic layer with a saturated aqueous solution of sodium chloride (20ml), it was dried with anhydrous magnesium sulfate. After the solventwas distilled off under reduced pressure, the obtained residue waspurified by silica gel column chromatography to obtain the objectedethyl(3-methyl-4-nitrobenzylamino)acetate [0.9 g, ¹H NMR (CDCl₃, ppm);1.2 (3H, t), 2.6 (3H, s), 3.4 (2H, s), 3.9 (2H, s), 4.2 (2H, q), 4.8(2H, s), 7.2-8.1 (3H, m)].

Synthesis Example 15 Starting Material Synthesis

4-(trifluoromethyl)phenylisocyanate (0.83 g) was added to a diethylether solution (50 ml) of ethyl(3-methyl-4-nitrobenzylamino)acetate (0.9g) and the mixture was stirred vigorously at room temperature for 7hours. By filtering the crystals a crude productethyl[1-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)ureido]acetate(0.8 g) was obtained and used in the next reaction without purification.

Synthesis Example 16 Starting Material Synthesis

Acetic acid solution (10 ml) ofethyl[1-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)ureido]acetate(0.5 g) and concentrated hydrochloric acid (3 ml) was refluxed for 5hours. After adding water (50 ml) the mixture was extracted with ethylacetate. After washing the organic layer with water and a saturatedaqueous solution of sodium chloride, it was dried with anhydrousmagnesium sulfate. After the solvent was distilled off under reducedpressure, the obtained residue was purified by silica gel columnchromatography to obtain the objected1-(3-methyl-4-nitrobenzyl)-3-(4-trifluoromethylphenyl)imidazolidin-2,4-dione[0.3 g, ¹H NMR (CDCl₃, ppm); 2.7 (3H, s), 4.0 (2H, s), 4.8 (2H, s),7.2-8.2 (7H, m)].

Synthesis Example 17 Starting Material Synthesis

4-Chloromethyl-2-methyl-1-nitrobenzene (1.9 g), aminoacetaldehydedimethyl acetal (6.3 g) and potassium carbonate (6.2 g) were mixed inacetonitrile (200 ml) and the mixture was refluxed for 20 hours. Afteradding water the mixture was extracted with ethyl acetate. After washingthe organic layer with a saturated aqueous solution of sodium chloride,it was dried with anhydrous magnesium sulfate. After the solvent wasdistilled off under reduced pressure, the obtained residue was purifiedby silica gel column chromatography to obtain the objected(2,2-dimethoxyethyl)-3-(methyl-4-nitrobenzyl)amine [2.5 g, ¹H NMR(CDCl₃, ppm); 2.6 (3H, s), 2.8 (2H, d), 3.5 (6H, s), 3.9 (2H, s), 4.6(1H, m), 7.2-8.1 (4H, m)].

Synthesis Example 18 Starting Material Synthesis

(2,2-Dimethoxyethyl)-3-(methyl-4-nitrobenzyl)amine (1.2 g) was dissolvedin ether (50 ml), to which 4-(trifluoromethyl)phenyl isocyanate (1.3 g)was added at room temperature, and the mixture was stirred vigorouslyfor 7 hours. After finishing the reaction, water was added to themixture and it was extracted with ethyl acetate. After drying theorganic layer with anhydrous magnesium sulfate, the solvent wasdistilled off under reduced pressure to obtain a crude product1-(2,2-dimethoxyethyl)-1-(3-metyl-4-nitrobenzyl)-4-(trifluoromethylphenyl)urea(1.8 g), which was used in the next reaction without purification.

Synthesis Example 19 Starting Material Synthesis

1-(2,2-Dimethoxyethyl)-1-(3-methyl-4-nitrobenzyl)-3-(4-(trifluoromethylphenyl)urea(1.8 g) was dissolved in THF (5 ml), to which 50% aqueous solution oftrifluoroacetic acid (20 ml), and the mixture was stirred at roomtemperature. After finishing the reaction and adding water, the mixturewas extracted with ethyl acetate. After washing the organic layer withwater and a saturated aqueous solution of sodium chloride, it was driedwith anhydrous magnesium sulfate. After the solvent was distilled offunder reduced pressure, the obtained residue was purified by silica gelcolumn chromatography to obtain the objected1-(3-methyl-4-nitrobenzyl)-3-(4-(trifluoromethylphenyl)-1,3-dihydroimidazol-2-one[1.2 g, ¹H NMR (CDCl₃, ppm); 2.6 (3H, s), 4.9 (2H, s), 6.4 (1H, d), 6.7(1H, d), 7.2-8.1 (7H, m)].

Biological Test Example 1 Test Against Larva of Spodoptera litura

Preparation of Test Agent:

Solvent: Dimethylformamide 3 parts by weight

Emulsifier: Polyoxyethylene alkyl phenyl ether 1 part by weight

In order to make an appropriate formulation of an active compound, 1part by weight of the active compound was mixed with the above-mentionedamount of solvent containing the above-mentioned amount of emulsifierand the mixture was diluted with water to a prescribed concentration.

Test Method:

Leaves of sweet potato were soaked in the test agent diluted to aprescribed concentration with water, dried in the air and put in a dishof 9 cm diameter. 10 larvae of Spodoptera litura at the third instarwere placed on the leaves and kept in a room at the constant temperatureof 25° C. After 2 and 4 days further leaves of sweet potato were addedand after 7 days the number of dead larvae was counted and the rate ofdeath was calculated.

In this test the results of 2 dishes at 1 section were averaged.

Test Results:

As specific examples the compounds of the compound no. 2-7,2-35, 2-67,2-71, 2-72, 2-96, 2-140, 2-141, 2-142, 2-147, 2-173, 2-176, 2-181,2-182, 2-270, 2-283, 2-293, 2-323, 2-333 and 2-337 showed 100% of rateof death at 20 ppm concentration of effective component.

Biological Test Example 2 Test Against Larva of Cnaphalocrocis medinalisGuenee

Test Method:

Rice seedlings (cultivar: Tamanishiki) of 4-5 leaf stage, planted in avinyl pot (9 cm diameter) were sprayed with the diluted aqueous solutionof the prescribed concentration of the active compound prepared in thesame manner as in the above mentioned Biological Test Example 1. Afterdrying, top ⅓ part of the leaves of the plants was cut and put into aPetri-dish (9 cm diameter), in which a piece of filter paper (9 cmdiameter) was laid and moistened. Five larvae of Cnaphalocrocismedinalis at the second instar were released in the Petri-dish and thedish was placed in a room at the constant temperature of 25° C. After 2and 4 days, another ⅓ part of the plant leaves was cut and added to thedish. After seven days, the number of dead larvae was counted and therate of death was calculated. In this test the results of 2 dishes at 1treatment were averaged.

Test Results:

As specific examples the compounds of the compound no. 2-12, 2-17, 2-50,2-54, 2-140, 2-141, 2-154, 2-172, 2-173, 2-234, 2-248, 2-253, 2-256,2-310, 2-333, 2-337, 4-8,4-15 and 4-16 showed 100% of rate of death at20 ppm concentration of effective component.

Formulation Example 1 Granule

To a mixture of 10 parts of the compound of the present invention (o.2-7), 30 parts of bentonite (montmorillonite), 58 parts of talc and 2parts of ligninsulfonate salt, 25 parts of water are added, wellkneaded, made into granules of 10-40 mesh by an extrusion granulator anddried at 40-50° C. to obtain granules.

Formulation Example 2 Granules

95 Parts of clay mineral particles having particle diameter distributionin the range of 0.2-2 mm are put in a rotary mixer. While rotating it 5parts of the compound of the present invention (No. 2-173) are sprayedtogether with a liquid diluent, wetted uniformly and dried at 40-50° C.to obtain granules.

Formulation Example 3 Emulsifiable Concentrate

30 Parts of the compound of the present invention (No. 2-140), 55 partsof xylene, 8 parts of polyoxyethylene alkyl phenyl ether and 7 parts ofcalcium alkylbenzenesulfonate are mixed and stirred to obtain anemulsifiable concentrate.

Formulation Example 4 Wettable Powder

Parts of the compound of the present invention (No. 2-333), 80 parts ofa mixture of white carbon (hydrous amorphous silicon oxide fine powders)and powder clay (1:5), 2 parts of sodium alkylbenzenesulfonate and 3parts of sodium alkylnaphthalenesulfonate-formalin-condensate arecrushed and mixed to make a wettable powder.

Formulation Example 5 Water Dispersible Granule

Parts of the compound of the present invention (No. 2-337), 30 parts ofsodium ligninsulfonate, 15 parts of bentonite and 35 parts of calcineddiatomaceous earth powder are well mixed, added with water, extrudedwith 0.3 mm screen and dried to obtain water dispersible granules.

1-7. (canceled)
 8. A phthalamide derivative of formula (I)

wherein X represents hydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,nitro, cyano, C₁-C₆-alkylsulfonyloxy, C₁-C₆-haloalkylsulfonyloxy,phenylsulfonyloxy, C₁-C₆-alkylthio-C₁-C₆-alkyl,C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl,C₁-C₆-alkylsulfonylamino, bis(C₁-C₆-alkylsulfonyl)amino, orC₁-C₆-alkoxy-carbonyl, n represents 1, 2, 3, or 4, Y representshydrogen, halogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy,C₁-C₆-haloalkoxy, C₁-C₆-alkylthio, C₁-C₆-haloalkylthio, or cyano, mrepresents 1, 2, 3, or 4, R¹ represents C₁-C₈-alkyl that is optionallymono- or polysubstituted by substituents selected from the groupconsisting of cyano, nitro, C₁-C₆-alkylaminosulfonyl,N,N-di(C₁-C₆-alkyl)aminosulfonyl, C₁-C₆-alkylsulfonylamino,N—C₁-C₆-alkylsulfonyl-N—C₁-C₆-alkylamino, C₁-C₆-alkyl-carbonylamino,halo-C₁-C₆-alkyl, N—C₁-C₆-alkyl-carbonyl-N—C₁-C₆-alkylamino,C₁-C₆-alkylthio-carbonylamino,N—C₁-C₆-alkylthiocarbonyl-N—C₁-C₆-alkylamino,C₁-C₆-alkoxyimino-C₁-C₆-alkyl, C₁-C₆-alkyl-aminocarbonyl,N,N-di(C₁-C₆-alkyl)aminocarbonyl, C₁-C₆-alkyl-aminothiocarbonyl,N,N-di(C₁-C₆-alkyl)-aminothiocarbonyl, C₁-C₆-alkoxy-carbonylamino,C₁-C₆-alkoxy-carbonyl-C₁-C₆-alkylamino, C₁-C₆-alkylamino-carbonyloxy,N,N-di(C₁-C₆-alkyl)amino-carbonyloxy, C₁-C₆-alkoxy-thiocarbonylamino,C₁-C₆-alkoxy-thiocarbonyl-C₁-C₆-alkylamino,C₁-C₆-alkylamino-thiocarbonyloxy,N,N-di(C₁-C₆-alkyl)amino-thiocarbonyloxy, C₁-C₆-alkylthio-carbonylamino,C₁-C₆-alkylthiocarbonyl-C₁-C₆-alkylamino, C₁-C₆-alkylamino-carbonylthio,N,N-di(C₁-C₆-alkyl)amino-carbonylthio,C₁-C₆-alkylthio-thiocarbonylamino,C₁-C₆-alkylthio-thiocarbonyl-C₁-C₆-alkylamino,C₁-C₆-alkylamino-thiocarbonylthio,N,N-di(C₁-C₆-alkyl)amino-thiocarbonylthio, C₃-C₆-cycloalkyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl,C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, and C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl; orrepresents C₃-C₈-cycloalkyl that is optionally substituted bysubstituents selected from the group consisting of C₁-C₄-alkyl,C₁-C₄-alkylthio, and C₁-C₂-alkylthio-C₁-C₂-alkyl, R² represents hydrogenor C₁-C₆-alkyl, R³ represents hydrogen or C₁-C₆-alkyl, A¹ representsstraight chain or branched chain C₁-C₈-alkylene, C₁-C₈-haloalkylene,C₂-C₈-alkenylene, C₂-C₈-haloalkenylene, C₂-C₈-alkynylene,C₂-C₈-haloalkynylene, C₁-C₈-alkylene-amino,C₁-C₈-alkylene(C₁-C₆-alkylamino), C₁-C₈-alkyleneoxy, orC₁-C₈-alkylenethio, r represents 0 or 1, A² represents straight chain orbranched chain C₁-C₈-alkylene, C₁-C₈-haloalkylene, C₂-C₈-alkenylene,C₂-C₈-haloalkenylene, C₂-C₈-alkynylene, or C₂-C₈-haloalkynylene, srepresents 0 or 1, Q represents a 5- or 6-membered heterocyclic groupcontaining 1 to 4 heteroatoms selected from 0 to 4 nitrogen atoms, 0 to1 oxygen atom, and 0 to 1 sulphur atom, with the proviso that Q does notsimultaneously contain an oxygen atom and a sulphur atom, wherein theheterocyclic group optionally has one to three

one to three

one

or one

 as ring constituents and optionally is substituted with one or moreidentical or different substituents W¹, W¹ represents halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy,C₁-C₆-haloalkylthio, C₁-C₆-haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl,C₃-C₆-cycloalkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl,C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, or C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, Erepresents phenyl, biphenyl, naphthyl, pyridyl, pyridazinyl,pyrimidinyl, pyrazinyl, thienyl, furyl, or pyrrolyl, each of which isoptionally substituted with one or more identical or differentsubstituents W², and W² represents halogen, nitro, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio,C₁-C₆-haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆-cycloalkyl,C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, orC₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, or two adjacent substituents W²together represent C₃-C₅-alkylene, C₃-C₅-haloalkylene,oxy-C₂-C₄-alkylene, oxy-C₂-C₄-haloalkylene, C₂-C₄-alkyleneoxy,C₂-C₄-haloalkyleneoxy, C₁-C₃-alkylenedioxy, or C₁-C₃-haloalkylenedioxy.9. A compound according to claim 8, wherein X represents hydrogen,halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, nitro, cyano,C₁-C₄-alkylsulfonyloxy, C₁-C₄-haloalkylsulfonyloxy, phenylsulfonyloxy,C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl,C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl, C₁-C₄-alkylsulfonylamino,bis(C₁-C₄-alkylsulfonyl)amino, or C₁-C₄-alkoxy-carbonyl, n represents 1,2, 3, or 4, Y represents hydrogen, halogen, C₁-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-haloalkylthio, or cyano, m represents 1, 2, 3, or 4, R¹ representsC₁-C₆-alkyl that is optionally mono- or polysubstituted by substituentsselected from the group consisting of cyano, nitro,C₁-C₄-alkylaminosulfonyl, N,N-di(C₁-C₄-alkyl)aminosulfonyl,C₁-C₄-alkylsulfonylamino, N—C₁-C₄-alkylsulfonyl-N—C₁-C₄-alkylamino,C₁-C₄-alkyl-carbonylamino, halo-C₁-C₄-alkyl,N—C₁-C₄-alkyl-carbonyl-N—C₁-C₄-alkylamino,C₁-C₄-alkylthio-carbonylamino,N—C₁-C₄-alkylthiocarbonyl-N—C₁-C₄-alkylamino,C₁-C₄-alkoxyimino-C₁-C₄-alkyl, C₁-C₄-alkyl-aminocarbonyl,N,N-di(C₁-C₄-alkyl)aminocarbonyl, C₁-C₄-alkyl-aminothiocarbonyl,N,N-di(C₁-C₄-alkyl)-aminothiocarbonyl, C₁-C₄-alkoxy-carbonylamino,C₁-C₄-alkoxy-carbonyl-C₁-C₄-alkylamino, C₁-C₄-alkylamino-carbonyloxy,N,N-di(C₁-C₄-alkyl)amino-carbonyloxy, C₁-C₄-alkoxy-thiocarbonylamino,C₁-C₄-alkoxy-thiocarbonyl-C₁-C₄-alkylamino,C₁-C₄-alkylamino-thiocarbonyloxy,N,N-di(C₁-C₄-alkyl)amino-thiocarbonyloxy, C₁-C₄-alkylthio-carbonylamino,C₁-C₄-alkylthio-carbonyl-C₁-C₄-alkylamino,C₁-C₄-alkylamino-carbonylthio, N,N-di(C₁-C₄-alkyl)amino-carbonylthio,C₁-C₄-alkylthio-thiocarbonylamino,C₁-C₄-alkylthio-thiocarbonyl-C₁-C₄-alkylamino,C₁-C₄-alkylamino-thiocarbonylthio,N,N-di(C₁-C₄-alkyl)amino-thiocarbonylthio, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl,C₁-C₄-alkylsulfinyl-C₁-C₄-alkyl, and C₁-C₄-alkylsulfonyl-C₁-C₄-alkyl; orrepresents C₃-C₆-cycloalkyl that is optionally substituted byC₁-C₂-alkyl, C₁-C₂-alkylthio or C₁-C₂-alkylthio-C₁-C₂-alkyl, R²represents hydrogen or C₁-C₄-alkyl, R³ represents hydrogen orC₁-C₄-alkyl, A¹ represents straight chain or branched chainC₁-C₆-alkylene, C₁-C₆-haloalkylene, C₂-C₆-alkenylene,C₂-C₆-haloalkenylene, C₂-C₆-alkynylene, C₂-C₆-haloalkynylene,C₁-C₆-alkylene-amino, C₁-C₆-alkylene(C₁-C₄-alkylamino),C₁-C₆-alkyleneoxy, or C₁-C₆-alkylenethio, r represents 0 or 1, A²represents straight chain or branched chain C₁-C₆-alkylene,C₁-C₆-haloalkylene, C₂-C₆-alkenylene, C₂-C₆-haloalkenylene,C₂-C₆-alkynylene, or C₂-C₆-haloalkynylene, s represents 0 or 1, Qrepresents pyridinylene, pyridazinylene, pyrimidinylene, orpyrazinylene, each of which is optionally substituted with one or moreidentical or different substituents W¹, or further represents a group

 wherein the bond marked with * connects with A¹ and the bond markedwith # connects with A² or the bond marked with # connects with A¹ andthe bond marked with * connects with A², W¹ represents halogen,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl,C₁-C₆-alkylsulfonyl, C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy,C₁-C₆-haloalkylthio, C₁-C₆-haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl,C₃-C₆-cycloalkyl, C₁-C₆-alkylthio-C₁-C₆-alkyl,C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, Erepresents phenyl, biphenyl, naphthyl, pyridyl, pyridazinyl,pyrimidinyl, pyrazinyl, thienyl, furyl, or pyrrolyl, each of groups isoptionally substituted with one or more identical or differentsubstituents W², W² represents halogen, nitro, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₆-alkylsulfinyl, C₁-C₆-alkylsulfonyl,C₁-C₆-haloalkyl, C₁-C₆-haloalkoxy, C₁-C₆-haloalkylthio,C₁-C₆-haloalkylsulfinyl, C₁-C₆-haloalkylsulfonyl, C₃-C₆-cycloalkyl,C₁-C₆-alkylthio-C₁-C₆-alkyl, C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, orC₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, or two adjacent substituents W²together represent C₃-C₅-alkylene, C₃-C₅-haloalkylene,oxy-C₂-C₄-alkylene, oxy-C₂-C₄-haloalkylene, C₂-C₄-alkyleneoxy,C₂-C₄-haloalkyleneoxy, C₁-C₃-alkylenedioxy, or C₁-C₃-haloalkylenedioxy,W³ represents hydrogen or has the same definition as substituent W¹, prepresents 0, 1, or 2, and q represents 0, 1, 2 or
 3. 10. A process forthe preparation of compounds of formula (I) according to claim 8comprising (a) for compounds of formula (I) in which R² representshydrogen, reacting a compound of formula (II)

wherein R¹, X, and n have the same definitions as given for formula (I)in claim 8, with a compound of formula (III)

wherein R³, Y, m, A¹, r, Q, A², s, and E have the same definition asgiven for formula (I) in claim 8, in the presence of inert solvents, or(b) for compounds of formula (I) in which R³ represents hydrogen,reacting a compound of formula (IV)

wherein X, n, Y, m, A¹, r, Q, A², s, and E have the same definition asgiven for formula (I) in claim 8, with a compound of formula (V)

wherein R¹ and R² have the same definition as given for formula (I) inclaim 8, in the presence of inert solvents and optionally in thepresence of a base, or (c) reacting a compound of formula (VI)

wherein X, n, R¹ and R² have the same definition as given for formula(I) in claim 8, with a compound of formula (III),

wherein R³, Y, m, A¹, r, Q, A², s and E have the same definition asgiven for formula (I) in claim 8, in the presence of inert solvents, or(d) for compounds of formula (I) in which R³ represents hydrogen,reacting a compound of formula (VII)

wherein X, n, Y, m, A¹, r, Q, A², s, and E have the same definition asgiven for formula (I) in claim 8, with a compound of formula (V),

wherein R¹ and R² have the same definition as given for formula (I) inclaim 8, in the presence of inert solvents, or (e) reacting a compoundof formula (VII)

wherein X, n, R³, Y, m, A¹, r, Q, A², s, and E have the same definitionas given for formula (I) in claim 8, with a compound of formula (V),

wherein R¹ and R² have the same definition as given for formula (I) inclaim 8, in the presence of inert solvents, or (f) for compounds offormula (I) in which R¹ represents C₁-C₆-alkylsulfinyl-C₁-C₆-alkyl, orC₁-C₆-alkylsulfonyl-C₁-C₆-alkyl, reacting a compound of formula (If)

wherein R^(1f) represents C₁-C₆-alkylthio-C₁-C₆-alkyl, and X, n, R², R³,Y, m, A¹, r, Q, A², s and E have the same definition as given forformula (I) in claim 8, with an oxidizing agent in the presence of inertsolvents.
 11. A pesticide comprising one or more compounds of formula(I) according to claim
 8. 12. A method of combating harmful insectscomprising allowing an effective amount of a compound of formula (I)according to claim 8 to act on pests and/or their habitat.
 13. A processfor preparing compositions for combating harmful insects comprisingmixing one or more compounds of formula (I) according to claim 8 withone or more extenders and/or surface active agents.